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

HRID 2361406노트

반응식

HRID 2361406 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)=[C:13]([CH3:33])[N:12]=[C:11]([C:34](=[O:36])[NH2:35])[C:7]=3[NH:8]2)=[CH:4][CH:3]=1.I[Si](C)(C)C>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:34]([NH2:35])=[O:36])=[N:12][C:13]=2[CH3:33])[CH:20]=[CH:19][CH:18]=1

참가 물질

4

반응물 2

HCID 85247Trimethylsilyl iodideHCID 70651685benzyl (3-(7-bromo-1-carbamoyl-3-methyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenyl)carbamate

생성물 1

HCID 679952474-(3-amino-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxamide수율 50%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of benzyl (3-(7-bromo-1-carbamoyl-3-methyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenyl)carbamate (1.10 g, 2.02 mmol) in acetonitrile (100 mL) at 0° C. was added iodotrimethylsilane (1.10 mL, 8.10 mmol) dropwise. The mixture was stirred at room temperature for 1.5 h. After concentration, diethylamine (2 mL) and ethyl acetate (150 mL) were added to the residue. The mixture was washed with water (2×40 mL), washed with brine (40 mL), and dried over anhydrous sodium sulfate. Concentration under reduced pressure followed by purification by flash silica gel chromatography using a mixture of ethyl acetate in hexane (20%-35%-50%) afforded 4-(3-amino-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxamide (0.411 g, 1.00 mmol, 50% yield) as a tan solid. LC/MS M+1=409.1 and 411.1.

후처리

  1. concentrationAfter concentration, diethylamine (2 mL) and ethyl acetate (150 mL)
  2. additionwere added to the residue
  3. washThe mixture was washed with water (2×40 mL)
  4. washwashed with brine (40 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationConcentration under reduced pressure
  7. customfollowed by purification by flash silica gel chromatography
  8. additiona mixture of ethyl acetate in hexane (20%-35%-50%)

출처 및 근거

ORD 기록
ord-92d8aa786db04b7a9e7f2cc69ba61c67
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685969B2

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