1H-indole-6-carboxylic acid → 4-t-Butyldimethylsilyloxy-N2-(4-t-butylbenzoyl)-N1-(6-indolylcarbonyl)-1,2-benzenediamine

HRID 842392Notes

Reaction equation

HRID 842392 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([NH:16][C:17](=[O:28])[C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=2)[C:12]([NH2:15])=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C:38](O)=[O:39])[CH:36]=2)[CH:31]=[CH:30]1>>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([NH:16][C:17](=[O:28])[C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=2)[C:12]([NH:15][C:38]([C:35]2[CH:36]=[C:37]3[C:32]([CH:31]=[CH:30][NH:29]3)=[CH:33][CH:34]=2)=[O:39])=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 5952301H-indole-6-carboxylic acidHCID 117951904-t-butyldimethylsilyloxy-N2-(4-t-butylbenzoyl)-1,2-benzenediamine

Product 1

HCID 537844544-t-Butyldimethylsilyloxy-N2-(4-t-butylbenzoyl)-N1-(6-indolylcarbonyl)-1,2-benzenediamineYield 50%

Procedure

Using the procedure described in Example 9, Part C, 4-t-butyldimethylsilyloxy-N2-(4-t-butylbenzoyl)-1,2-benzenediamine (1.15 g, 2.9 mmol) and indole-6-carboxylic acid (0.46 g, 2.9 mmol) yielded 780 mg (50%) of the title compound.

Sources & evidence

ORD record
ord-22156cfed986481881659d4cd3fdf853
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

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