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

HRID 379723Notes

Reaction equation

HRID 379723 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-2eedbdddd43344a7a0cec60b0c1f8e49
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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