Sodium borohydride → HCID 22676727, compound

Participants

Reaction Steps

Sodium borohydride (38 mg, 1.0 mmol) was added to a stirred solution of ethyl 3-[3-(cyclopropylmethoxy)phenyl]-1-(3-methoxybenzyl)-5-(2-oxoethoxy)-1H-indole-2-carboxylate (Example 136, 380 mg, 0.74 mmol) in methanol (10 mL). The reaction was stirred for 2 h and then the reaction was quenched with water (100 mL). The product was extracted with ethyl acetate (3×40 mL) and then the combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to leave 363 mg (95%) of product containing some impurities. The material was used in the next reaction without further purification. The product had: 1H NMR (300 MHz, acetone-D6) δ 7.34-7.46 (m, 3 H), 7.16 (dd, 1 H), 6.93-7.02 (m, 4 H), 6.65-6.81 (m, 3 H), 5.78 (s, 2 H), 3.82-4.23 (m, 9 H), 3.69 (s, 3 H), 1.24-1.34 (m, 1 H), 1.02 (t, 3 H), 0.60-0.70 (m, 2 H), 0.34-0.44 (m, 2 H).

Provenance & Evidence