Sodium hydride → HCID 23678526, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (6.8 mg, 0.28 mmol) was added to a cooled (0° C.) and stirred solution of 3-(4-tert-butylphenyl)-5-[2-(cyclopropylmethoxy)ethyl]-1-(3-methoxybenzyl)-1H-indole-2-carboxylic acid (Example 275, 145 mg, 0.283 mmol) in tetrahydrofuran (10 mL). The cold bath was removed and the mixture was stirred 2 h. Concentration in vacuo left 148 mg (98%) of the desired product. The product had: 1H NMR (300 MHz, acetone-D6) δ 7.63 (d, 2 H), 7.47 (s, 1 H), 7.34 (d, 2 H), 7.18 (d, 1 H), 7.09(dd, 1 H), 6.96 (dd, 1 H), 6.91 (s, 1 H), 6.85 (d, 1 H), 6.69 (dd, 1 H), 5.75 (s, 2 H), 3.66 (s, 3 H), 3.56 (t, 2 H), 3.22 (d, 2 H), 2.84 (t, 2 H), 1.32 (s, 9 H), 0.89-1.05 (m, 1 H), 0.35-0.45 (m, 2 H), 0.07-0.17 (m, 2 H); mass spectroscopy gave M+2H+−Na=512.2 (calcd exact mass for C33H36NNaO4=533.25).

Provenance & Evidence