Dimethylformamide → 5-methoxy-1-methyl-1H-indole

HRID 488535

반응식

HRID 488535 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[CH2:12]1N2CCN(CC2)C1.CN(C=O)C>CCOC(C)=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[CH:6]2

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 9237DabcoHCID 138725-Methoxyindole

생성물 1

HCID 8198645-methoxy-1-methyl-1H-indole수율 967%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
92.5 °C

실험 절차

To a solution of 5-methoxyindole (1.0 g, 6.79 mmol) in DMC (10 mL), DABCO (0.076 g, 0.68 mmol) is added followed by DMF (2 mL). The resulting solution is heated to 90-95° C. for 7 h. The reaction is cooled to RT, and diluted with EtOAc (40 mL) and H2O (40 mL). The organic layer is separated and washed in sequence with H2O (50 mL), 10% aqueous citric acid (2×40 mL) and H2O (4×40 mL). The organic layer is dried over anhydrous Na2SO4, filtered and concentrated under vacuum to give 5-methoxy-1-methylindole (about 1.06 g, 97%) as a solid: 1H NMR (CDCl3) δ7.21 (d, 1H), 7.09 (d, 1H), 7.00 (d, 1H), 6.87 (dd, 1H) 6.39 (d, 1H), 3.84 (s, 3H), 3.73 (s, 3H); 13C NMR (CDCl3) δ153.9, 132.1, 129.3, 128.7, 111.8, 109.9, 102.4, 100.3, 55.9, 32.9; MS m/z 161 [M+1]+.

후처리

  1. temperatureThe reaction is cooled to RT
  2. customThe organic layer is separated
  3. washwashed in sequence with H2O (50 mL), 10% aqueous citric acid (2×40 mL) and H2O (4×40 mL)
  4. dry with materialThe organic layer is dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-5fac3eec3983420ca8f8724f9f103b84
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06972336B2

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