tert-butyl 5-bromo-2,3-dihydro-1H-indole-1-carboxylate → HCID 68454059, compound

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Reaction Steps

Following the procedure of steps 2 and 4 of Example 1, 5-bromo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (0.48 g, 1.6 mmol) was coupled with 3-benzyl-piperazine-1-carboxylic acid tert-butyl ester to give 5-(2-benzyl-4-tert-butoxycarbonyl-piperazin-1-yl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester, which was then deprotected by reaction with TFA to afford 5-(2-benzyl-piperazin-1-yl)-2,3-dihydro-1H-indole (0.16 g) as a yellow foam; 1H NMR (300, MHz, CDCl3) δ 7.24-7.10 (m, 3H), 7.17-1.01 (m, 2H), 6.96 (d, J=2.2 Hz, 1H), 6.82 (dd, J=8.2, 2.2 Hz, 1H), 3.61-3.46 (m, 3H), 3.20-2.69 (m, 7H), 2.84-2.72 (m, 2H), 2.56 (dd, J=10.5, 13.6 Hz, 1H); MS (M+H)=294.

Provenance & Evidence