Cesium carbonate → 4-fluoro-N-(3-methoxy-5-(prop-1-en-2-yl)pyridin-2-yl)benzenesulfonamide

HRID 594122노트

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HRID 594122 반응식
[B-](F)(F)(F)[C:2]([CH3:4])=[CH2:3].[K+].Br[C:10]1[CH:11]=[C:12]([O:27][CH3:28])[C:13]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[N:14][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.O.ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:26][C:23]1[CH:24]=[CH:25][C:20]([S:17]([NH:16][C:13]2[C:12]([O:27][CH3:28])=[CH:11][C:10]([C:2]([CH3:4])=[CH2:3])=[CH:15][N:14]=2)(=[O:19])=[O:18])=[CH:21][CH:22]=1

참가 물질

9

반응물 3

HCID 10796Cesium carbonateHCID 23670158Potassium (prop-1-en-2-yl)trifluoroborateHCID 89876109HCID 89876109, 화합물

생성물 1

HCID 898762164-fluoro-N-(3-methoxy-5-(prop-1-en-2-yl)pyridin-2-yl)benzenesulfonamide수율 64.6%

시약·촉매·용매 5

HCID 11776Triphenylphosphine촉매HCID 24290Palladium Chloride촉매HCID 962Water용매2회HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
140 °C

실험 절차

Potassium trifluoro(prop-1-en-2-yl)borate (53.3 mg, 0.360 mmol), N-(5-bromo-3-methoxypyridin-2-yl)-4-fluorobenzenesulfonamide (130 mg, 0.360 mmol), caesium carbonate (352 mg, 1.080 mmol), palladium(II) chloride (1.276 mg, 7.20 μmol) and triphenylphosphine (5.66 mg, 0.022 mmol) were added to a microwave vial and suspended in tetrahydrofuran (THF) (2 mL) and water (0.2 mL). The reaction vessel was sealed and heated by microwaves to 140° C. for 30 minutes. After cooling, the mixture was diluted with dichloromethane (DCM) (5 mL) and water (5 mL), then passed through a celite column. The aqueous phase was washed with further DCM (5 mL) then the organics separated using a hydrophobic frit and concentrated in vacuo to give the crude product. This was purified by flash silica (Si) chromatography (0-50% ethyl acetate-cyclohexane gradient) to give the title product (75 mg). LCMS (2 min, formic) Rt 1.0 min, m/z (ES+) 323 (M+H).

후처리

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. washThe aqueous phase was washed with further DCM (5 mL)
  4. customthe organics separated
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThis was purified by flash silica (Si) chromatography (0-50% ethyl acetate-cyclohexane gradient)

출처 및 근거

ORD 기록
ord-6dafa5cf9e0e455ab1f9e850ab4cb224
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242972B2

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