Trifluoroacetic acid → HCID 86703327, 화합물

HRID 2410012노트

반응식

HRID 2410012 반응식
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]3([CH3:15])[CH2:14][CH2:13]3)[NH:9]2)=[CH:5][C:4]=1[CH3:16].[CH:17]([C:19]1[N:24]=[C:23]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=[CH:21][CH:20]=1)=O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:17][C:19]3[N:24]=[C:23]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3([CH3:15])[CH2:13][CH2:14]3)[NH:9]2)=[CH:5][C:4]=1[CH3:16]

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 12575850Methyl 6-formylpyridine-2-carboxylateHCID 86703326HCID 86703326, 화합물

생성물 1

HCID 86703327HCID 86703327, 화합물수율 69.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 6-methoxy-5-methyl-2-(1-methylcyclopropyl)-1H-indole (586 mg) and methyl 6-formylpyridine-2-carboxylate (450 mg) in dichloromethane (13.6 mL) was added triethylsilane (1.30 mL) under ice-cooling. Trifluoroacetic acid (0.313 mL) was added dropwise thereto, and the mixture was stirred under ice-cooling for 30 minutes and then at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was suspended in methanol. The precipitate was collected by filtration, washed with methanol, and then dried under reduced pressure at 40° C. to obtain the title compound (688 mg). 1H-NMR (CDCl3) δ ppm: 0.66-0.72 (2H, m), 0.80-0.86 (2H, m), 1.31 (3H, s), 2.19 (3H, s), 3.84 (3H, s), 4.05 (3H, s), 4.48 (2H, s), 6.78 (1H, s), 7.00 (1H, s), 7.04-7.10 (1H, m), 7.59 (1H, t, J=7.8 Hz), 7.79 (1H, br s), 7.91-7.97 (1H, m). ESI-MS (m/z): 365 (M+H)+

후처리

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with methanol
  9. customdried under reduced pressure at 40° C.

출처 및 근거

ORD 기록
ord-5a170f2ead594c0d9de1558374f64f5b
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815903B2

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