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Triethylamine → 5-Bromo-3-[(1,1-dioxidotetrahydro-3-thienyl)methyl]-1H-indole-7-carboxamide

HRID 656059
ノート
印刷プレビュー

反応式

HRID 656059 の反応式
C[N:2](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[Br:30][C:31]1[CH:32]=[C:33]2[C:37](=[C:38]([C:40](O)=[O:41])[CH:39]=1)[NH:36][CH:35]=[C:34]2[CH2:43][CH:44]1[CH2:48][CH2:47][S:46](=[O:50])(=[O:49])[CH2:45]1.N.CO>ClCCl>[Br:30][C:31]1[CH:32]=[C:33]2[C:37](=[C:38]([C:40]([NH2:2])=[O:41])[CH:39]=1)[NH:36][CH:35]=[C:34]2[CH2:43][CH:44]1[CH2:48][CH2:47][S:46](=[O:50])(=[O:49])[CH2:45]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21705897Ammonia methanolHCID 593327835-bromo-3-[(1,1-dioxidotetrahydro-3-thienyl)methyl]-1H-indole-7-carboxylic acid

生成物 1

HCID 593326215-Bromo-3-[(1,1-dioxidotetrahydro-3-thienyl)methyl]-1H-indole-7-carboxamide収率 33.6%

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒

反応条件

温度
20 °C

実験手順

TBTU (5.68 g, 17.68 mmol) and triethylamine (1.79 g, 17.68 mmol) were added to a solution of 5-bromo-3-[(1,1-dioxidotetrahydro-3-thienyl)methyl]-1H-indole-7-carboxylic acid (3.28 g, 8.84 mmol) in dichloromethane (100 mL). After the mixture was stirred for 0.5 h at 20° C., NH3/MeOH was added into the solution, and stirring continued for 2 h. The mixture was washed with water and extracted with EtOAc. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (petroleum:ethyl acetate=10:1 to 5:1 to 2:1), giving 1.1 g (33.6%) of the title compound.

後処理

  1. stirringstirring
  2. waitcontinued for 2 h
  3. washThe mixture was washed with water
  4. extractionextracted with EtOAc
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel (petroleum:ethyl acetate=10:1 to 5:1 to 2:1)

出典と根拠

ORDレコード
ord-2645c6c8a78d47cfb62d345a4029a5ac
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08071584B2

反応ノート

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