Trimethylsilyl iodide → 4-(3-amino-2-methylphenyl)-7-bromo-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361363노트

반응식

HRID 2361363 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3[C:14]([C:15]4[C:16]([CH3:32])=[C:17]([NH:21]C(=O)OCC5C=CC=CC=5)[CH:18]=[CH:19][CH:20]=4)=[CH:13][N:12]=[C:11]([C:33](=[O:35])[NH2:34])[C:7]=3[NH:8]2)=[CH:4][CH:3]=1.I[Si](C)(C)C.C(OCC)(=O)C.CCCCCC>C(#N)C>[NH2:21][C:17]1[C:16]([CH3:32])=[C:15]([C:14]2[C:6]3[C:5]4[C:9](=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=4)[NH:8][C:7]=3[C:11]([C:33]([NH2:34])=[O:35])=[N:12][CH:13]=2)[CH:20]=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 85247Trimethylsilyl iodideHCID 21226206Ethyl acetate hexaneHCID 67994872Benzyl 3-(7-bromo-1-carbamoyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate

생성물 1

HCID 679947214-(3-amino-2-methylphenyl)-7-bromo-9H-pyrido[3,4-b]indole-1-carboxamide수율 52.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of benzyl 3-(7-bromo-1-carbamoyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate (0.65 g, crude from the previous step) in acetonitrile (80 mL) at 0° C. was added iodotrimethylsilane (0.67 mL, 4.91 mmol) dropwise. The mixture was stirred at room temperature for 1.5 hr, and then concentrated under vacuum. To the residue was added diethylamine (2 mL) and ethyl acetate (150 ml). The mixture was washed with water (2×40 mL) and brine (40 mL), and dried over anhydrous MgSO4. The desired product (0.243 g, 52.6% yield over two steps) was isolated as a beige solid by ISCO (40 g silica gel, solid loading, 40-70% ethyl acetate/hexane).

후처리

  1. concentrationconcentrated under vacuum
  2. additionTo the residue was added diethylamine (2 mL) and ethyl acetate (150 ml)
  3. washThe mixture was washed with water (2×40 mL) and brine (40 mL)
  4. dry with materialdried over anhydrous MgSO4

출처 및 근거

ORD 기록
ord-47dfa53861d44a33b7cac2bb2e50fc92
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685969B2

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