Water → 3-Acetylamino-6-chloro-2-(3-methoxybenzoyl)indole

HRID 379729Notes

Reaction equation

HRID 379729 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:12](=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1.N1C=CC=CC=1.[C:28](Cl)(=[O:30])[CH3:29].O>ClCCl.C(OCC)C>[C:28]([NH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:12](=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)(=[O:30])[CH3:29]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 183680283-Amino-6-chloro-2-(3-methoxybenzoyl)indole

Product 1

HCID 183681043-Acetylamino-6-chloro-2-(3-methoxybenzoyl)indole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-6-chloro-2-(3-methoxybenzoyl)indole (Example 18, 413 mg, 1.37 mmol) in dichloromethane (20 ml) was added pyridine (0.33 ml, 4.12 mmol) and acetyl chloride (0.14 ml, 2.06 mmol). After stirring for 0.5 h, water (1 ml) and diethyl ether (100 ml) were added, and the mixture washed consecutively with 1N aqueous HCl (50 ml×2) and saturated aqueous sodium bicarbonate (50 ml×2). The organic layer was dried (MgSO4) and solvent removed. The resultant residue was purified by flash chromatography eluting with ethyl acetate/hexane (1:2) to afford the title compound as an oil. Crystallization from ethanol/hexane to give 260 mg (55%) of title compound. m.p.: 161-162° C. 1H-NMR (CDCl3) δ: 9.92 (1H, br s), 8.32 (1H, br s), 8.22 (1H, d, J=9.2 Hz), 7.47 (1H, dd, J=7.7 and 8.1 Hz), 7.37-7.26 (3H, m), 7.18-7.08 (1H, m), 7.10 (1H, dd, J=1.6 and 9.0 Hz), 3.88 (3H, s), 2.25 (3H, s)

Workup

  1. washthe mixture washed consecutively with 1N aqueous HCl (50 ml×2) and saturated aqueous sodium bicarbonate (50 ml×2)
  2. dry with materialThe organic layer was dried (MgSO4) and solvent
  3. customremoved
  4. customThe resultant residue was purified by flash chromatography
  5. washeluting with ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-5b637e7fed394ef799ad953188f659ec
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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