Potassium Carbonate → 4-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamide

HRID 216323ノート

反応式

HRID 216323 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[CH3:9][O:10][N:11]([CH3:23])[C:12]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)=[O:13].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CO.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:8][C:5]1[CH:6]=[CH:7][C:2]([C:17]2[CH:18]=[CH:19][C:14]([C:12]([N:11]([O:10][CH3:9])[CH3:23])=[O:13])=[CH:15][CH:16]=2)=[N:3][CH:4]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27831712-Bromo-5-fluoropyridineHCID 36744904-(N,O-Dimethylhydroxylaminocarbonyl)phenylboronic acid

生成物 1

HCID 866384894-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamide

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 21867641Toluene methanol溶媒

反応条件

温度
90 °C

実験手順

Palladium tetrakis(triphenylphosphine) (1.38 g, 1.2 mmol) was added to a degassed, ambient temperature solution of 2-bromo-5-fluoropyridine (5 g, 28.4 mmol) and (4-{[methoxy(methyl)amino]carbonyl}phenyl)boronic acid (5 g, 23.9 mmol) and potassium carbonate (4.3 g, 31.1 mmol) in toluene/methanol (9.5:1) (105 mL). After stirring at 90° C. for 1.5 hr, the reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-80% ethyl acetate/hexane afforded 4-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamide.

後処理

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0b6748ef8bb54121b161784cbe96fee9
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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