2-Bromo-5-fluoropyridine → 2,2-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-N-methoxy-N-methylacetamide

HRID 216416ノート

反応式

HRID 216416 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:16])([F:15])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])=[CH:4][CH:3]=1.Br[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=1.C[Sn](C)C.C[Sn](C)C>O1CCOCC1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:15][C:8]([F:16])([C:5]1[CH:6]=[CH:7][C:2]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=2)=[CH:3][CH:4]=1)[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10]

参加物

7

反応物 3

HCID 27831712-Bromo-5-fluoropyridineHCID 6327618HexamethylditinHCID 866385182-(4-bromophenyl)-2,2-difluoro-N-methoxy-N-methylacetamide

生成物 1

HCID 866385172,2-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-N-methoxy-N-methylacetamide

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

Palladium tetrakis(triphenylphosphine) (236 mg, 0.20 mmol) was added to a degassed, ambient temperature solution of 2-(4-bromophenyl)-2,2-difluoro-N-methoxy-N-methylacetamide (600 mg, 2.05 mmol), 2-bromo-5-fluoropyridine (360 mg, 2.05 mmol) and hexamethylditin (670 mg, 2.05 mmol) in 1,4-dioxane (20 mL). After stirring at reflux overnight, the reaction mixture was diluted with water and extracted with methylene chloride and ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-60% ethyl acetate/hexane afforded 2,2-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-N-methoxy-N-methylacetamide.

後処理

  1. temperatureat reflux overnight
  2. extractionextracted with methylene chloride and ethyl acetate
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-1b70c91b52474c9d99a038ea40fafc7f
出典データセット
uspto-grants-2012_06
特許番号
US08193228B2

反応ノート

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