4-Carboxyphenylboronic Acid → 4-({4-[(5-chloro-1H-indol-2-yl)sulphonyl]piperazin-1-yl}carbonyl)phenyl boronic acid

HRID 28397

反応式

HRID 28397 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([S:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)(=[O:13])=[O:12])=[CH:5]2.[C:20]([C:23]1[CH:28]=[CH:27][C:26]([B:29]([OH:31])[OH:30])=[CH:25][CH:24]=1)(O)=[O:21].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([S:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]([C:23]3[CH:24]=[CH:25][C:26]([B:29]([OH:31])[OH:30])=[CH:27][CH:28]=3)=[O:21])[CH2:16][CH2:15]1)(=[O:13])=[O:12])=[CH:5]2

参加物

5

反応物 3

HCID 3121834-Carboxyphenylboronic AcidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 227105715-chloro-2-(piperazine-1-sulfonyl)-1H-indole

生成物 1

HCID 693073894-({4-[(5-chloro-1H-indol-2-yl)sulphonyl]piperazin-1-yl}carbonyl)phenyl boronic acid収率 56%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

5-Chloro-2-(piperazin-1-ylsulphonyl)-1H-indole (5.42 g, 18.1 mmol) was added to a solution of 4-carboxyphenyl boronic acid (3.00 g, 18.1 mmol) N,N-diisopropylethylamine (2.34 g, 18.1 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (5.81 g, 18.1 mmol) in 80 mL N,N-dimethylformamide, the mixture was stirred for 2 hours at room temperature. N,N-Dimethylformamide was removed in vacuo and the crude was purified by flash chromatography three times (dichloromethane/methanol, 100-98/2) to give 4-({4-[(5-chloro-1H-indol-2-yl)sulphonyl]piperazin-1-yl}carbonyl)phenyl boronic acid as a colourless solid (56% yield).

後処理

  1. customN,N-Dimethylformamide was removed in vacuo
  2. customthe crude was purified by flash chromatography three times (dichloromethane/methanol, 100-98/2)

出典と根拠

ORDレコード
ord-4b86f7cb244e4996a5c483f75e27e621
出典データセット
uspto-grants-2008_09
特許番号
US07419979B2

関連ノート

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