5-Bromo 2-hydroxy benzonitrile was obtained from Apollo Chemical. Ethyl. bromoacetate and N-methylpiperazine were purchased from Aldrich.

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1 Supplemental Information Synthesis of Compound A 5-Bromo 2-hydroxy benzonitrile was obtained from Apollo Chemical. Ethyl bromoacetate and N-methylpiperazine were purchased from Aldrich. 5-Bromo-2- fluoropyridine was obtained from VWR. Bromo 3-methoxypropane was obtained from Maybridge. 1-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole was obtained from Frontier Scientific. 1H-NMR spectral data was collected on a Bruker 400 MHz instrument. Step 1

2 To a stirred solution of 5-bromo 2-hydroxy benzonitrile (1) (37 g, 187 mmol) in acetone (1.3 L), sodium carbonate (29.7 g, 280 mmol, 1.5 equiv.) and ethyl bromoacetate (46.8 g, 280 mmol, 1.5 equiv.) were added at 25 C. The reaction mixture was refluxed overnight. The reaction mixture was concentrated under reduced pressure, and then crude was quenched by 1N HCl, and extracted with ethyl acetate. The organic layer was separated and washed with brine and dried over sodium sulfate, filtered and concentrated to get the uncyclized adduct. The resulting residue was dissolved in EtOH, a solution of NaOEt/EtOH (2 equiv., 21%) was added and heated at 90 C during 1h (complete conversion). The solution was cooled down to RT, concentrated to approx. 50 ml, filtered, the collected yellow solid was rinsed with Et 2 O and dried (2, 37g, 59%). Step 2 To a solution of compound 2 (37 g, 130 mmol) in toluene (1 L) and acetonitrile (750 ml) was added ethylchloroformate (105 ml, 8.5 equiv.) at RT. Then reaction mixture was stirred at 100ºC for 6 hrs. The reaction mixture was cooled to RT and the solid was filtered, washed with hexanes and dried under suction (3, 31 g, 67%). Step 3 To a stirred solution of 3 (28 g, 77 mmol) in DMSO (280 ml) were added cesium carbonate (51 g, 157 mmol, 2 equiv.) and 1-bromo-3-methoxypropane (18 g, 118 mmol, 1.5 equiv.) at 0 C and the reaction mixture was stirred for about 2 hours at 25 C. Reaction mixture was quenched with ice-water and extracted with ethyl acetate. Organic layer was washed with brine dried over anhydrous sodium sulfate filtered and

3 concentrated under reduced pressure. The crude was purified by chromatography on silica gel under moderate pressure ( flash chromatography ), product was eluted with 10% ethyl acetate + Pet-ether to afford compound 4 (28.8 g, 86%). Step 4 5-Bromo-2-fluoropyridine (1.3 ml, 12.9 mmol, 1.2 equiv.) and the bromide 4 (4.59 g, 10 mmol) were placed in an oven pre-dried 25 ml round-bottom flask, flushed with nitrogen and THF (58 ml) was added. The mixture was stirred under nitrogen at 25 C until a solution was formed. The mixture was stirred, then it was cooled in a dry-ice/acetone bath (-78 C) for 15 min. The n-buli solution (2.5M in hexanes, 5 ml, 11.8 mmol, 1.1 equiv.) was added dropwise over 120 minutes. The mixture was then stirred at -78 C for 1.5hr. 10 drops of AcOH were added, stirred 5 minutes; silica gel was poured into the mixture. Volatiles were evaporated under reduced pressure. The crude product was purified by Medium Pressure Automated Silica gel chromatography (0-30% EtOAc in hexanes gradient) to afford 5 (3.64 g, 71%). Step 5 Intermediate 5 (1.92 g, 4.00 mmloles, 1.0 eq) was dissolved in anhydrous DMSO (19 ml) and to the solution was added N-methylpiperazine (0.488 ml, 4.40 mmoles, 1.1 eq) followed by triethylamine (0.61 ml, 4.40 mmoles, 1.1 eq). The solution was heated to 50 C and stirred for 30 min. Solution was taken up in EtOAc (300 ml), washed with H 2 O(1X), brine(3x), dried(na 2 SO 4 ), filtered and concentrated to afford 6 (2.13 g, 95%). Step 6

4 The starting material 6 (2.13 g, 3.8 mmoles, 1.0 eq) and ammonium acetate (12.28 g) were combined and heated at 150 o C for 30 min. The reaction was followed by UPLC and after completion the mixture was cooled to room temperature and worked up. Water was added to the reaction followed by NaOH (10 N) until the ph of the mixture was basic (yellow precipitate formed). The ph of the aqueous layer was adjusted to about 10 and extracted with dichloromethane (3X). This organic layer was dried (MgSO 4 ), filtered and concentrated to afford more of the target product 7 (1.87 g, 95%). Step 7 7 (50 mg, mmoles, 1.0 eq) and 1-methyl-4-(4,4,5,5-tetramethyl- [1,3,2]dioxaborolan-2-yl)-1H-pyrazole (44 mg, 0.21 mmoles, 2.2 eq) were combined in a 2-5 ml microwave reaction vessel along with K 2 CO 3 (40 mg, 0.29 mmoles, 3.0 eq) and CsF (44 mg, 0.29 mmoles, 3 eq). The mixture was dissolved in dioxane (1.86 ml)/water (0.47 ml) and degassed under argon for 15 min. Finally the catalyst Pd(dppf)Cl 2 (9.5 mg, 0.01 mmoles, 0.12 eq) was added and the reaction subjected to the microwave at 135 o C for 25 min. The solution was concentrated, the crude mixture was dissolved in AcOH, filtered through an Acrodisc filter and purified by Preparative-HPLC to afford 8 (42.5 mg, 85%). Spectral data 1H NMR (400 MHz, DMSO-d6) δ (m, 1H), 8.54 (dd, J=2.45, 9.10 Hz, 1H), 8.35 (d, J=1.17 Hz, 1H), 8.21 (s, 1H), 7.99 (dd, J=1.80, 8.80 Hz, 1H), 7.99 (br. d, J=1.80 Hz, 1H), 7.90 (s, 1H), 7.20 (d, J=9.19 Hz, 1H), 4.67 (d, J=13.30 Hz, 2H), 4.51 (t,

5 J=15.30 Hz, 2H), 3.92 (s, 3H), (m, 4H), 3.14 (br. s., 2H), (m, 2H); HPLC (RP, SunFire column, Water+0.1%TFA:Acetonitrile eluent gradient) : Rt = 3.47 min., >99.5% purity (254 nm UV detector); MS (ESI+) : (M+H). High Throughput Screening Method The NcRTI biochemical assay was screened against our entire corporate compound collection, which numbered over one million compounds using the final assay conditions described in Materials and Methods. The high-throughput screen (HTS) was performed using the Allegro screening system (Zymark Corporation;now PerkinElmer) which is a modular linear robotic system (Armstrong JW A Review of Linear Robotic Systems for High Throughput Screening -- New Developments Result in More Flexibility and Lower Cost. Journal of Laboratory Automation 4: 28). Each step of the HTS, including all plate movement, was controlled by separate Allegro modules. Compound plates, containing 2 µl of compound (0.5 mg/ml) in 100 % DMSO, were diluted 25-fold with assay buffer and 10 µl was transferred into a black Greiner assay plate. HIV-1 RT was diluted to 8 nm in assay buffer and 10 µl of RT was added to diluted compound and pre-incubated for 5 min at room temperature. 20 µl assay buffer containing poly(ra)/oligo(dt)15 and ATP was added and assay plates were covered with a plastic seal and incubated for 60 min at 37 C in a dry oven (with controlled humidity). The final concentration of DMSO in the assay was 1%. All assay plates contained negative controls, consisting of 1% DMSO and positive control (no test inhibitor). Finaly, 40 µl Quant-IT Picogreen (diluted 1:375 into 20 mm Tris/HCl-25 mm EDTA, ph8.0) was

6 added and assay plates were incubated for 5 min at room temperature following a 10 seconds shake. Fluorescence was measured using a Wallac Victor II plate reader using wavelengths specific for fluorescein. The activity of the test compounds were reported as percent activity of the DMSO control (percent of control, POC). The HTS campaing resulted in an average Z of Using a selected hit cutoff (for each assay plate) equivalent to 3 standard deviation of the negative control wells, the hit rate was 0.8% (7375 hits). The average hit cutoff for the complete HTS campaign was 79 POC. Hits were retested at a single concentration identical to that initially tested in the HTS. Compounds whose activity was confirmed were then tested in concentration response mode. All HTS data was analyzed using Activity Base (ID Business Solutions Ltd.).

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