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

HRID 2361406ノート

反応式

HRID 2361406 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-92d8aa786db04b7a9e7f2cc69ba61c67
出典データセット
uspto-grants-2014_04
特許番号
US08685969B2

反応ノート

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