Cesium carbonate → 6-(4-Fluoro-3-(trifluoromethyl)phenyl)picolinaldehyde

HRID 1472923노트

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HRID 1472923 반응식
Br[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][C:12]=1[C:20]([F:23])([F:22])[F:21].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=2)=[CH:13][C:12]=1[C:20]([F:21])([F:22])[F:23]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 27570096-Bromopyridine-2-carbaldehydeHCID 177500514-Fluoro-3-(trifluoromethyl)benzeneboronic acid

생성물 1

HCID 848199696-(4-Fluoro-3-(trifluoromethyl)phenyl)picolinaldehyde수율 91%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

To a solution of 6-bromopicolinaldehyde (1.00 g, 5.38 mmol) in dioxane (30 mL) at ambient temperature was added 4-fluoro-3-(trifluoromethyl)phenylboronic acid (1.11 g, 5.38 mmol), 2M cesium carbonate (8.0 mL, 16 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.220 g, 0.269 mmol). The mixture was degassed (3× vacuum/purge N2), then heated at 80° C. overnight. After cooling to room temperature the mixture was concentrated and the residue partitioned between water and CH2Cl2. The organic extract was concentrated and purified by chromatography (10% ethyl acetate:hexanes) to provide 1.31 g (91%) of the title compound. MS (DCI+) m/z 270 (M+H).

후처리

  1. customThe mixture was degassed
  2. custom(3× vacuum/purge N2)
  3. temperatureAfter cooling to room temperature the mixture
  4. concentrationwas concentrated
  5. customthe residue partitioned between water and CH2Cl2
  6. extractionThe organic extract
  7. concentrationwas concentrated
  8. custompurified by chromatography (10% ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-85a26152321e4d208c3397dbc1cb8f62
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012651B2

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