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

HRID 2354573Notes

Reaction equation

HRID 2354573 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH:27]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N:28]3[CH2:29][CH2:30][N:25]([C:23]([O:22][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:24])[CH2:26][CH:27]3[CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 21865438tert-butyl 5-bromo-2,3-dihydro-1H-indole-1-carboxylateHCID 44118664tert-Butyl 3-benzylpiperazine-1-carboxylate

Product 1

HCID 68454059HCID 68454059, compound

Procedure

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.

Sources & evidence

ORD record
ord-48f14e413ae7447f872351216d229edf
Source dataset
uspto-grants-2010_07
Patent number
US07754721B2

Reaction notes

Loading…