Potassium Carbonate → HCID 67195169, 화합물

HRID 882247

반응식

HRID 882247 반응식
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](Br)=[CH:11][CH:12]=2)[C@H:7]([NH:15][C:16](=[O:21])[O:17][CH:18]([CH3:20])[CH3:19])[CH2:6][C@@H:5]1[CH3:22])(=[O:3])[CH3:2].CC1(C)C(C)(C)OB([C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.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.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.[Pd]>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:31]3[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:15][C:16]([O:17][CH:18]([CH3:20])[CH3:19])=[O:21])[CH2:6][C@@H:5]1[CH3:22])(=[O:3])[CH3:2]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2773500Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 52935020HCID 52935020, 화합물

생성물 1

HCID 67195169HCID 67195169, 화합물수율 81%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
100 °C

실험 절차

To a solution of isopropyl ((2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamate (5 g, 13.54 mmol) and methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (3.90 g, 14.89 mmol) in DME (50 mL) and water (10.0 mL) were successively added palladium tetrakis(triphenylphosphine) (1.565 g, 1.354 mmol) and potassium carbonate (5.61 g, 40.6 mmol). The resulting mixture was stirred at 100° C. for 1 h, whereupon it was allowed to cool down to room temperature and was filtered through Celite™. The filtrated was concentrated in vacuo and the residue was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc (×3) and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude compound was purified by flash chromatography on a silica gel cartridge (50 g) eluting with EtOAc in cyclohexane (5-60%). The appropriate fractions were combined and concentrated under reduced pressure to give methyl 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (4.64 g, 81%) as a white gum. LCMS (Formate, 2 min), Rt=1.09 min, MH+=425.

후처리

  1. temperatureto cool down to room temperature
  2. filtrationwas filtered through Celite™
  3. concentrationThe filtrated was concentrated in vacuo
  4. customthe residue was partitioned between EtOAc and water
  5. extractionThe aqueous phase was extracted with EtOAc (×3)
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude compound was purified by flash chromatography on a silica gel cartridge (50 g)
  11. washeluting with EtOAc in cyclohexane (5-60%)
  12. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2feadce1d6b04167b119a864fb3c90a8
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993554B2

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