4-tert-Butylphenylboronic acid → 1-benzyl-5-[(4-tert-butylphenyl)amino]-3-phenyl-1H-indole-2-carboxylic acid

HRID 2055742Notes

Reaction equation

HRID 2055742 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([C:18]([O:20]CC)=[O:19])=[C:5]2[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:29]([C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)([CH3:32])([CH3:31])[CH3:30]>>[CH2:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][C:36]3[CH:37]=[CH:38][C:33]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:34][CH:35]=3)=[CH:10][CH:9]=2)[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:6]1[C:18]([OH:20])=[O:19])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 27343204-tert-Butylphenylboronic acidHCID 69229300ethyl 5-amino-1-benzyl-3-phenyl-1H-indole-2-carboxylate

Product 1

HCID 113749121-benzyl-5-[(4-tert-butylphenyl)amino]-3-phenyl-1H-indole-2-carboxylic acid

Procedure

The title compound was prepared from ethyl 5-amino-1-benzyl-3-phenyl-1H-indole-2-carboxylate and 4-tert-butylbenzeneboronic acid according to the procedure of Example 1 Step 3 as a pale green solid: 1H NMR (DMSO-d6) δ 1.22 (s, 9 H), 5.81 (s, 2 H), 6.87 (d, J=6.7 Hz, 2 H), 7.10-7.50 (m, 15 H), 12.85 (br s, 1 H); MS (ESI) m/z 475 (MH+); MS (ESI) m/z 473 ([M-H]−); Anal. calcd. for C32H30N2O2.0.5H2O: C, 79.78; H, 6.46; N, 6.02. Found: C, 79.42; H, 6.28; N, 6.01.

Sources & evidence

ORD record
ord-6fced8c0eb9546bda550bbc07259c76e
Source dataset
uspto-grants-2008_02
Patent number
US07332521B2

Reaction notes

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