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

HRID 1472923ノート

反応式

HRID 1472923 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-85a26152321e4d208c3397dbc1cb8f62
出典データセット
uspto-grants-2015_04
特許番号
US09012651B2

反応ノート

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