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

HRID 2192288
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HRID 2192288 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매
HCID 8857
Ethyl Acetate
용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cba1fbfedf524d85bb931a9d3a1205f7
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08329725B2

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