Sodium cyanoborohydride → HCID 178485596, compound

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Reaction Steps

To a solution of product (5-B) (0.4 g 1.6 mmol) in DCE (20 mL) was added product (3-C) (0.25 g, 1.6 mmol) at rt under argon. The reaction was stirred for about 5 h, and then NaBH3CN (0.5 g, 8 mmol) was added and stirred overnight. The reaction was quenched by saturated NH4Cl (20 mL) and extracted with DCM/MeOH (20:1 v/v, 20 mL×2). The combined organic phases were dried over Na2SO4 and concentrated and purified by Prep-HPLC to give compound 4 (22 mg, 5%) as a white solid. 1H NMR (300 MHz, d-DMSO): δ 13.04 (br, 1H), 8.14-7.32 (m, 9H), 7.04-6.36 (m, 4H), 5.98-5.85 (m, 2H), 4.47 (d, 2H), 2.72 (d, 3H). LC-MS (M+H)+=387. 1H-NMR (in DMSO), LC-MS, MS, and HPLC (column: Thermo, 2.4 μm, 4.6×100 mm; mobile phase: H2O (0.05% TFA)-ACN (0.05% TFA), ACN from 10% to 100% in eight minutes; total flow rate: 1.0 mL/min) spectroscopy experiments were conducted to provide the data in FIGS. 3A-3C and FIGS. 4A-4B for compound 4.

Provenance & Evidence