Benzyl chloroformate → Benzyl 1H-indol-6-ylcarbamate

HRID 2361256ノート

反応式

HRID 2361256 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:10])[CH:8]=2)[CH:3]=[CH:2]1.[C:11](Cl)(=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.CCCCCC>O1CCCC1.C(OCC)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=2)[CH:3]=[CH:2]1

参加物

7

反応物 4

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 2560966-AminoindoleHCID 21226206Ethyl acetate hexane

生成物 1

HCID 67994742Benzyl 1H-indol-6-ylcarbamate収率 52.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 1H-indol-6-amine (1.0 g, 7.57 mmol), benzyl carbonochloridate (1.421 mL, 9.46 mmol), and potassium carbonate (1.307 g, 9.46 mmol) in tetrahydrofuran (50 mL) was stirred at room temperature for 16 hr. The mixture was diluted with ethyl acetate (150 mL) and insoluble material was removed by filtration. The filtrate was washed sequentially with saturated NaHCO3 solution (50 mL) and brine (50 mL). The organic solution was dried over anhydrous MgSO4. The desired product (1.05 g, 3.94 mmol, 52.1% yield) was isolated as a white solid by ISCO (120 g silica gel, solid loading, 5-30% ethyl acetate/hexane).

後処理

  1. customwas removed by filtration
  2. washThe filtrate was washed sequentially with saturated NaHCO3 solution (50 mL) and brine (50 mL)
  3. dry with materialThe organic solution was dried over anhydrous MgSO4

出典と根拠

ORDレコード
ord-0887b02b50bd46cfae99b2696a258b2d
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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