Pyridine → 3-Acetylamino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole

HRID 379723ノート

反応式

HRID 379723 の反応式
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]=1[C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1C=CC=CC=1.[C:31](Cl)(=[O:33])[CH3:32]>ClCCl>[C:31]([NH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]=1[C:17](=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)(=[O:33])[CH3:32]

参加物

5

反応物 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 183678333-Amino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole

生成物 1

HCID 183680413-Acetylamino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole収率 54%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-amino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole (300 mg, 0.88 mmol; example 1, step 2) in a mixture of dichloromethane (10 ml) and pyridine (0.08 ml, 0.96 mmol) was added acetyl chloride (0.07 ml, 0.96 mmol). After stirring for 4 h, the mixture was partitioned between 10% aqueous citric acid (50 ml) and diethyl ether (100 ml). The organic extract was washed consecutively with water (50 ml), saturated sodium bicarbonate (50 ml), water (50 ml) and brine (50 ml). After drying (MgSO4) and removal of solvent, the crude product was purified by flash chromatography eluting with ethyl acetate/hexane (1:1) to afford 183 mg (54%) of the titled compound as a yellow oil.

後処理

  1. customthe mixture was partitioned between 10% aqueous citric acid (50 ml) and diethyl ether (100 ml)
  2. extractionThe organic extract
  3. washwas washed consecutively with water (50 ml), saturated sodium bicarbonate (50 ml), water (50 ml) and brine (50 ml)
  4. customAfter drying
  5. custom(MgSO4) and removal of solvent
  6. customthe crude product was purified by flash chromatography
  7. washeluting with ethyl acetate/hexane (1:1)

出典と根拠

ORDレコード
ord-2eedbdddd43344a7a0cec60b0c1f8e49
出典データセット
uspto-grants-2001_10
特許番号
US06300363B1

反応ノート

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