Acetyl chloride → 4-(3-Bromo-4,5-dimethoxyphenyl)-2-methoxy-7-methyl-pyrrolo[2,3-h]chroman

HRID 1454003노트

반응식

HRID 1454003 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[C:17]4[CH:24]=[CH:23][N:22]([CH3:25])[C:18]4=[CH:19][CH:20]=3)[O:15][CH:14]([OH:26])[CH2:13]2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].[C:27](Cl)(=O)C.C(=O)(O)[O-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[C:17]4[CH:24]=[CH:23][N:22]([CH3:25])[C:18]4=[CH:19][CH:20]=3)[O:15][CH:14]([O:26][CH3:27])[CH2:13]2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 103872724-(3-Bromo-4,5-dimethoxyphenyl)-2-hydroxy-7-methyl-pyrrolo[2,3-h]chroman

생성물 1

HCID 100028974-(3-Bromo-4,5-dimethoxyphenyl)-2-methoxy-7-methyl-pyrrolo[2,3-h]chroman수율 58%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 4-(3-bromo-4,5-dimethoxyphenyl)-2-hydroxy-7-methyl-pyrrolo[2,3-h]chroman (5 mg; 0.012 mmol ) in methanol (0.5 ml) at 0° C. was added acetyl chloride (10 μl). The mixture was warmed to room temperature and stirred at this temperature for 3 h. Saturated sodium bicarbonate solution was added and the reaction mixture was extracted with dichloromethane. The extract was washed with saturated sodium chloride solution, dried and evaporated. The crude product was passed through bond-elute (hexane:ethyl acetate=9:1 as eluent), giving the title compound (3 mg; 58%). 1H NMR (acetone-d6): 7.14 (d, J=2.7 Hz) and 7.13 (d, J=2.9 Hz) (1H), 6.94-7.02 (m, 2H), 6.89 and 6.88 (d each, J=8.5 Hz, 1H), 6.50-6.57 (m, 2H), 5.32 (t, J=2.6 Hz) and 5.27 (dd, J=2.3, 7.6 Hz) (1H), 4.34 (dd, J=6.6, 9.5 Hz) and 4.27 (dd, J=6.0, 11.3 Hz) (1H), 3.85, 3.82, 3.81, 3.80, 3.79, 3.78 (s each, 9H), 3.59 and 3.50 (s each, 3H), 2.43 (ddd, J=2.3, 6.6, 13.3 Hz) and 2.12-2.30 (m) (2H).

후처리

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. washThe extract was washed with saturated sodium chloride solution
  3. customdried
  4. customevaporated
  5. washthrough bond-elute (hexane:ethyl acetate=9:1 as eluent)

출처 및 근거

ORD 기록
ord-549057ea24964e55abfab53bb3a9c267
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476741B2

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