Water → Methyl 2',3'-difluoro-5-(5-methylpyridin-2-yl)biphenyl-3-carboxylate

HRID 2278722ノート

反応式

HRID 2278722 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16](B3OC(C)(C)C(C)(C)O3)[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[N:6][CH:7]=1.Br[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:29]=1[F:35].C(=O)([O-])[O-].[Cs+].[Cs+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[F:34][C:30]1[C:29]([F:35])=[CH:28][CH:33]=[CH:32][C:31]=1[C:16]1[CH:17]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=2)[CH:9]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:15]=1

参加物

7

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27332601-Bromo-2,3-difluorobenzeneHCID 59432564Methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

生成物 1

HCID 58449385Methyl 2',3'-difluoro-5-(5-methylpyridin-2-yl)biphenyl-3-carboxylate

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

Into a 5 mL microwave vial were charged with methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (250 mg, 0.71 mmol), 1-bromo-2,3-difluorobenzene (273 mg, 1.42 mmol), cesium carbonate (1.15 g, 3.54 mmol), tetra-n-butylammonium iodide (261 mg, 0.71 mmol), POPd (35 mg, 0.071 mmol), water (0.5 mL) and N,N-dimethylformamide (3 mL). The reaction mixture was subjected to microwave irradiation at 150° C. for 10 mins. After cooling, the reaction mixture was extracted with ethylacetate. The organic layer was washed with brine, dried, and concentrated under reduced pressure to give the residue which was purified by silica gel column to yield the title compound.

後処理

  1. customirradiation at 150° C. for 10 mins
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with ethylacetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto give the residue which
  8. customwas purified by silica gel column

出典と根拠

ORDレコード
ord-5117508c65dd43a1af6590cbf3994f49
出典データセット
uspto-grants-2015_09
特許番号
US09133122B2

反応ノート

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