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Cesium carbonate → 5-(6-Trifluoromethyl-pyridin-3-yl)-2,3-dihydro-1H-indole

HRID 2192288
ノート
印刷プレビュー

反応式

HRID 2192288 の反応式
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][N:4]=1.Br[C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH2:19][CH2:18]2.C(=O)([O-])[O-].[Cs+].[Cs+]>O.CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]([F:13])([F:12])[C:3]1[N:4]=[CH:5][C:6]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][CH2:19][CH2:18]3)=[CH:7][CH:8]=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

7

反応物 3

HCID 10796Cesium carbonateHCID 34115665-BromoindolineHCID 251342782-(Trifluoromethyl)pyridine-5-boronic Acid

生成物 1

HCID 584082835-(6-Trifluoromethyl-pyridin-3-yl)-2,3-dihydro-1H-indole

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
100 °C

実験手順

1.6 g 2-(Trifluormethyl)pyridin-5-ylboronic acid, 1.66 g commercially available 5-Bromo-2,3-dihydro-1H-indole and 8.19 g cesium carbonate were dissolved in a mixture of 7 ml water and 21 ml dimethylformamide. The reaction mixture was degassed with argon and then 484 mg tetrakis(triphenylphosphine)palladium(0) were added and the mixture heated to 100° C. for two hours. The cooled reaction mixture was diluted with 200 ml ethyl acetate and washed with 100 ml water and brine. The organic layer was dried over MgSO4 and the solvent removed in vacuo. The resulting crude material was purified by purified by chromatography on silica gel to obtain 885 mg 5-(6-Trifluoromethyl-pyridin-3-yl)-2,3-dihydro-1H-indole.

後処理

  1. customThe reaction mixture was degassed with argon
  2. addition484 mg tetrakis(triphenylphosphine)palladium(0) were added
  3. customThe cooled reaction mixture
  4. washwashed with 100 ml water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent removed in vacuo
  7. customThe resulting crude material was purified
  8. customby purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-cba1fbfedf524d85bb931a9d3a1205f7
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08329725B2

反応ノート

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