Water → methyl 2-(1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)acetate

HRID 527444

반응식

HRID 527444 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][C:13]([O:15][CH3:16])=[O:14].[H-].[Na+].[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.O>CN(C=O)C>[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[C:6]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:7]2)=[O:25])=[CH:22][CH:21]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 85014-Chlorobenzoyl chlorideHCID 24758Sodium hydrideHCID 594955methyl 2-(5-methoxy-1H-indol-3-yl)acetate

생성물 1

HCID 57563309methyl 2-(1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)acetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Methyl 2-(5-methoxy-1H-indol-3-yl)acetate (60 mg, 0.27 mmol) and NaH (8 mg, 0.33 mmol) were stirred in anhydrous DMF (1 mL) at 0° C. under argon for 30 min, at which time 4-chlorobenzoyl chloride (57 mg, 0.33 mmol) was added. The reaction mixture was stirred overnight at room temperature and was then poured into cold water (2 mL). The organic compound was immediately extracted with dichloromethane (2×2 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified on silica (ethyl acetate/hexane gradient) and recrystallized from hexane. Yield: 18 mg (18%). C19H16ClNO4, Mr=357.79; 1H NMR (400 MHz, DMSO-d6) d: 3.61 (s, 3H), 3.78 (s, 2H), 3.81 (s, 3H), 7.00 (dd, J=2.4/9.0 Hz, 1H), 7.12 (d, J=2.4 Hz, 1H), 7.35 (s, 1H), 7.65-7.77 (m, 4H), 8.17 (d, J=8.8 Hz, 1H); LCMS (ESI) tR: 2.81 min (>99%, ELSD), m/z: 358.0 [M+1]+.

후처리

  1. additionwas added
  2. extractionThe organic compound was immediately extracted with dichloromethane (2×2 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on silica (ethyl acetate/hexane gradient)
  7. customrecrystallized from hexane

출처 및 근거

ORD 기록
ord-64547cd1dbe042d9896b7a22cb3b889b
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346803B2

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