Water → 3-Acetylamino-7-chloro-2-[(N-methoxy-N-methylamino)carbonyl]indole

HRID 379914Notes

Reaction equation

HRID 379914 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[C:6]([Cl:11])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13].N1C=CC=CC=1.[C:24](OC(=O)C)(=[O:26])[CH3:25].O>ClCCl>[C:24]([NH:1][C:2]1[C:10]2[C:5](=[C:6]([Cl:11])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 183680523-Amino-7-chloro-2-[(N-methoxy-N-methylamino)carbonyl]indole

Product 1

HCID 183681463-Acetylamino-7-chloro-2-[(N-methoxy-N-methylamino)carbonyl]indoleYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-7-chloro-2-[(N-methoxy-N-methylamino)carbonyl]indole (step 3, 287 mg, 1.1 mmol) in dichloromethane (10 ml) was added pyridine (2 ml) and acetic anhydride (0.16 ml, 1.7 mmol) at room temperature. After stirring for 3 h, the mixture was poured into water (100 ml) and extracted with ethyl acetate (150 ml). The organic layer was washed with 2N aquous HCl (100 ml), water (100 ml), saturated aqueous sodium bicarbonate (100 ml), brine (100 ml), and dried (MgSO4). After removal of solvent, the residue was purified by flash column chromatography eluting with ethyl acetate/hexane (1:101:1) to give 320 mg (98%) of the title compound.

Workup

  1. extractionextracted with ethyl acetate (150 ml)
  2. washThe organic layer was washed with 2N aquous HCl (100 ml), water (100 ml), saturated aqueous sodium bicarbonate (100 ml), brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. customAfter removal of solvent
  5. customthe residue was purified by flash column chromatography
  6. washeluting with ethyl acetate/hexane (1:101:1)

Sources & evidence

ORD record
ord-d7bdb0cbe23a475cac06196488ec4514
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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