(Pyridin-4-yl)boronic acid → HCID 86596815, compound

HRID 1678203Notes

Reaction equation

HRID 1678203 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]([C:25]3[CH:30]=[CH:29][C:28](I)=[CH:27][CH:26]=3)[C:16]3[C:21]([C:22]=2[CH:23]=[O:24])=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]([C:25]3[CH:30]=[CH:29][C:28]([C:35]4[CH:36]=[CH:37][N:32]=[CH:33][CH:34]=4)=[CH:27][CH:26]=3)[C:16]3[C:21]([C:22]=2[CH:23]=[O:24])=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 117529254-[3-formyl-1-(4-iodophenyl)-1H-indol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86596815HCID 86596815, compoundYield 70%

Procedure

4-[3-Formyl-1-(4-iodophenyl)-1H-indol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester is reacted with 4-pyridylboronic acid as described in Example 65 to afford 4-[3-formyl-1-[(4-pyridin-4-yl)-phenyl]-1H-indol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester (70% yield) as a yellow solid. ESI/MS 483 (M+1); NMR (CDCl3) 10.30 (1H, s); 8.76 (2H, d); 8.28 (1H, d, J=6 Hz); 7.89 (2H, d, J=9 Hz); 7.64 (5H, m); 7.20 (2H, m); 3.36 (8H, m); 1.58 (9H, s).

Sources & evidence

ORD record
ord-888e8b8f8c024bc79437b12e40a6c6d7
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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