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

HRID 216323노트

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HRID 216323 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 21867641Toluene methanol용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0b6748ef8bb54121b161784cbe96fee9
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193228B2

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