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

HRID 2361363ノート

反応式

HRID 2361363 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)=[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

参加物

5

反応物 3

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

生成物 1

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

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-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).

後処理

  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

出典と根拠

ORDレコード
ord-47dfa53861d44a33b7cac2bb2e50fc92
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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