Triethylamine → Methyl quinoline-7-carboxylate

HRID 14240

반응식

HRID 14240 반응식
FC(F)(F)C(O[C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1)=O.C(N(CC)CC)C.CN([CH:28]=[O:29])C.[CH3:30][OH:31]>>[N:13]1[C:14]2[C:9](=[CH:8][CH:7]=[C:6]([C:30]([O:29][CH3:28])=[O:31])[CH:15]=2)[CH:10]=[CH:11][CH:12]=1

참가 물질

4

반응물 3

HCID 8471TriethylamineHCID 21087171Quinolin-7-yl trifluoroacetateHCID 21901440N,N-dimethylformamide methanol

생성물 1

HCID 12554532Methyl quinoline-7-carboxylate

반응 조건

온도
60 °C

실험 절차

To a stirred solution of quinolin-7-yl trifluoroacetate (750 mg, 2.7 mmol), PdCl2(Ph3P) (95 mg, 0.14 mmol), and triethylamine (1.2 mL, 8.4 mmol) in 1:2 DMF/MeOH (39 mL) was degassed and sparged with CO, and the mixture was heated at 60° C. for 48 h. The mixture was cooled to room temperature, filtered through diatomaceous earth, and concentrated under reduced pressure. The residue was diluted with a 5% solution of LiCl, and washed with CHCl3 (3×250 mL). The combined organics were dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 3:1 ethyl acetate/hexanes) provided methyl quinoline-7-carboxylate (185 mg): ESI MS m/z 188 [M+H]+.

후처리

  1. customsparged with CO
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through diatomaceous earth
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was diluted with a 5% solution of LiCl
  6. washwashed with CHCl3 (3×250 mL)
  7. dry with materialThe combined organics were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification by flash column chromatography (silica, 3:1 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-80f411743c6a47c7bbddd39f6e9301b5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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