2-chloro-1-phenyl-1H-indole-3-carbaldehyde → 4-(3-formyl-1-phenyl-1H-indole-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 751363Notes

Reaction equation

HRID 751363 reaction equation
Cl[C:2]1[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:19]([O:23][C:24]([N:26]1[CH2:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][C:24]([N:26]1[CH2:32][CH2:31][CH2:30][N:29]([C:2]2[N:3]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]3[C:9]([C:10]=2[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

3

Reactant 2

HCID 3147932-chloro-1-phenyl-1H-indole-3-carbaldehydeHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 865968104-(3-formyl-1-phenyl-1H-indole-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl esterYield 87%

Procedure

2-Chloro-1-phenyl-1H-indole-3-carboxaldehyde is reacted with [1,4]diazepane-1-carboxylic acid tert-butyl ester as described in Example 1 to afford 4-(3-formyl-1-phenyl-1H-indole-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (87% yield) as a yellow solid. LC/MS MS 420 (M+H); RT 3.55 min; NMR (CDCl3): 10.25 (1H, s), 8.27 (1 H, d), 7.46-7.66 (3H, m), 7.37 (2H, d), 7.22-7.30 (1H, t), 7.16(1 H, t), 6.96 (1 H, d), 3.25-3.45 (8H, m), 1.56 (2H, m), 1.44(9H, s).

Sources & evidence

ORD record
ord-7bfcb767b51d4ca3b29dd14afda8abb7
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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