Sodium borohydride → HCID 71143644, compound

Participants

Reaction Steps

2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]-3-oxo-isoindoline-5-carbonitrile (130 mg, 0.1858 mmol) dissolved in a mixture of DCM (10 mL) and MeOH (5 mL) under N2. CoCl2 (48.25 mg, 0.3716 mmol) added then the reaction mixture cooled in an ice bath. NaBH4 (70 mg, 1.858 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 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, d), 3.50 (1H, sep), 3.88 (2H, s), 5.49 (2H, s), 7.65 (1H, d), 7.71 (1H, d), 7.84 (1H, s), 8.00 (2H, d), 8.51-8.53 (3H, m), 9.09 (1H, s) ppm; MS (ES+) 462.0.

Provenance & Evidence