Cesium carbonate → 2-[(1-Benzyl-2-ethyl-6,7,8,9-tetrahydro-1h-benz[g]indol-4-yl)oxy]acetic acid methyl ester

HRID 489113노트

반응식

HRID 489113 반응식
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([O:21][CH3:22])[CH:13]=[C:14]3[CH2:20][CH2:19][CH2:18][CH2:17][C:15]3=2)[CH:10]=[C:9]1[CH2:23][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.C(=O)([O-])[O-].[Cs+].[Cs+].BrC[C:37]([O:39][CH3:40])=[O:38]>C(Cl)Cl.O>[CH3:40][O:39][C:37](=[O:38])[CH2:22][O:21][C:12]1[CH:13]=[C:14]2[CH2:20][CH2:19][CH2:18][CH2:17][C:15]2=[C:16]2[C:11]=1[CH:10]=[C:9]([CH2:23][CH3:24])[N:8]2[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 25134Boron tribromideHCID 60984Methyl bromoacetateHCID 113361641-Benzyl-2-ethyl-4-methoxy-6,7,8,9-tetrahydro-1h-benz[g]indole

생성물 1

HCID 113149142-[(1-Benzyl-2-ethyl-6,7,8,9-tetrahydro-1h-benz[g]indol-4-yl)oxy]acetic acid methyl ester수율 63.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of 1-benzyl-2-ethyl-4-methoxy-6,7,8,9-tetrahydro-1H-benz[g]indole (660 mg, 2.07 mmol) in methylene chloride (10 mL) was cooled to 0° C. and treated with boron tribromide (0.38 mL, 4.0 mmol). The mixture was stirred for 10 min, poured into ice water, and extracted twice with methylene chloride. The combined methylene chloride layers were washed once with saturated sodium bicarbonate solution, dried (sodium sulfate), filtered, and concentrated in vacuo. The residue was dissolved in N,N-dimethylformamide (10 mL) and treated with cesium carbonate (652 mg, 2.00 mmol) and methyl bromoacetate (0.28 mL, 2.0 mmol) at room temperature for 3 h. The mixture was diluted with water and extracted three times with ether. The combined ether extracts were washed once with water, dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, methylene chloride) provided 479 mg (62%) of the title compound as an off-white solid. 1H NMR (CDCl3) δ 7.25 (m, 3H), 6.85 (d, J=7.6 Hz, 2H), 6.52 (s, 1H), 6.16 (s, 1H), 5.57 (s, 2H), 4.79 (s, 2H), 3.86 (s, 3H), 2.97 (m, 2H), 2.84 (m, 2H), 2.59 (q, J=7.3 Hz, 2H), 1.72 (m, 4H), 1.32 (t, J=7.3 Hz, 3H); MS ES+ m/e 378 (p+1); IR (CHCl3, cm1) 2830, 1756, 1732.

후처리

  1. extractionextracted twice with methylene chloride
  2. washThe combined methylene chloride layers were washed once with saturated sodium bicarbonate solution
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in N,N-dimethylformamide (10 mL)
  7. extractionextracted three times with ether
  8. washThe combined ether extracts were washed once with water
  9. dry with materialdried (magnesium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c2fd62053eea44aba55a9cdd87fe4a79
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06974831B2

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