Methanol → Methyl 2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline-6-carboxylate

HRID 1693075노트

반응식

HRID 1693075 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([CH3:18])([CH3:17])[C:13]([F:16])([F:15])[F:14])[CH:6]=[CH:5]2.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:55][OH:56].CN([CH:60]=[O:61])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:14][C:13]([F:16])([F:15])[C:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:55]([O:61][CH3:60])=[O:56])[CH:3]=2)[N:8]=1)([CH3:18])[CH3:17]

참가 물질

7

반응물 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 574581686-Bromo-2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline

생성물 1

HCID 57458169Methyl 2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline-6-carboxylate수율 88%

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

실험 절차

A mixture of 6-bromo-2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline (950 mg, 3.0 mmol), triethylamine (1.25 ml, 9.0 mmol), 1,3-bis(diphenylphosphino)propane (123 mg, 0.3 mmol), palladium acetate (67 mg, 0.3 mmol) and methanol (4.8 ml) in DMF (10 ml) was stirred at reflux under carbon monoxide (1 atm) for 16 hours. Then the reaction was quenched with saturated sodium bicarbonate aqueous solution and the product was extracted with ethyl acetate which was dried over sodium sulfate. Then, filtration, evaporation and purification through silica gel column chromatography, eluting with hexane/ethyl acetate (25:1), furnished the title compound (777 mg, 88% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.74 (6H, s), 4.00 (3H, s), 7.71 (1H, d, J=8.8 Hz), 8.14 (1H, d, J=8.8 Hz), 8.25 (1H, d, J=8.8 Hz), 8.28-8.32 (1H, m), 8.58-8.59 (1H, m). MS (ESI): m/z 298 (M+H)+.

후처리

  1. temperatureat reflux under carbon monoxide (1 atm) for 16 hours
  2. customThen the reaction was quenched with saturated sodium bicarbonate aqueous solution
  3. extractionthe product was extracted with ethyl acetate which
  4. dry with materialwas dried over sodium sulfate
  5. filtrationThen, filtration, evaporation and purification through silica gel column chromatography
  6. washeluting with hexane/ethyl acetate (25:1)

출처 및 근거

ORD 기록
ord-975bbb47cdb244bdb47516b2acc18bc0
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158650B2

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