Sodium Carbonate → N-[2-(2,2-difluoro-1,3-benzodioxol-4-yl)-4-methylphenyl]-2,2-dimethylpropanamide

HRID 1781244노트

반응식

HRID 1781244 반응식
Br[C:2]1[C:10]2[O:9][C:8]([F:12])([F:11])[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.B([C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[NH:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.CCCCCC>COCCOC.O.[Pd](Cl)Cl.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>[F:11][C:8]1([F:12])[O:7][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:16]3[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=3[NH:23][C:24](=[O:29])[C:25]([CH3:27])([CH3:26])[CH3:28])[C:10]=2[O:9]1

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 27732974-Bromo-2,2-difluoro-1,3-benzodioxoleHCID 19045057N-(2-borono-4-methylphenyl)-2,2-dimethylpropanamideHCID 21226206Ethyl acetate hexane

생성물 1

HCID 19045056N-[2-(2,2-difluoro-1,3-benzodioxol-4-yl)-4-methylphenyl]-2,2-dimethylpropanamide

시약·촉매·용매 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a mixture of the title compound of Step B (10.0 g, 42.2 mmol) and the title compound of Step A (4.96 g, 21.1 mmol) in ethylene glycol dimethyl ether (100 mL) were added a solution of sodium carbonate (4.47 g, 42.2 mmol) in water (25 mL) and bis(triphenylphosphine) palladium (II) chloride (740 mg, 1.05 mmol) at room temperature. The mixture was heated at reflux for 2 h and then allowed to come to room temperature. The solvent was removed under reduced pressure and the residue was suspended in water. The aqueous mixture was extracted with ethyl acetate three times. The organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure to obtain a brown liquid. Flash chromatography of the crude product on silica gel eluting with 1:6 ethyl acetate/hexane afforded the title compound of Step C, a compound of the invention, as a yellow oily solid (8 g, 55%). 1H NMR (CDCl3): δ1.12 (s,9H), 2.37 (s,3H), 7.1 (m,2H), 7.12 (s, 1H), 7.2 (t, 1H), 7.25 (m,1H), 7.3 (br s,1H), 7.9 (d, 1H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. customto come to room temperature
  4. customThe solvent was removed under reduced pressure
  5. extractionThe aqueous mixture was extracted with ethyl acetate three times
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto obtain a brown liquid

출처 및 근거

ORD 기록
ord-d18919271ba346f0943598126ca972e9
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05633218

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