Methanol → HCID 71143582, compound

Participants

Reaction Steps

2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]-1-oxo-isoindoline-4-carbonitrile (80 mg, 0.1143 mmol) dissolved in DCM (10 mL) and MeOH (5 mL) under N2. CoCl2 (29.68 mg, 0.2286 mmol) added and the reaction mixture cooled in an ice bath. NaBH4 (43 mg, 1.143 mmol) added in one portion. Ice bath removed and mixture stirred for 2 h then cooled in an ice bath and water (˜5 mL) added. Mixture diluted with DCM (˜20 mL) and stirred vigorously for 20 mins. Layers separated and aqueous phase extracted with DCM. Aqueous phase basified by addition of sat NaHCO3 solution and extracted with DCM (×2). Combined organics dried and concentrated to a brown foam. This material deprotected using Method E Step 2 to give the title compound after purification by hplc; 1H NMR (400 MHz, DMSO) δ 1.21 (6H, s), 3.50 (1H, sep), 4.03 (2H, s), 5.59 (2H, s), 7.56 (1H, t), 7.71 (2H, m), 8.01 (2H, d), 8.51 (1H, s), 8.54 (2H, d), 9.12 (1H, s) ppm; MS (ES+) 462.0.

Provenance & Evidence