Acetyl chloride → 3-Acetylamino-6-chloro-2-(pyridine-2-carbonyl)indole

HRID 379825Notes

Reaction equation

HRID 379825 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]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[O:13].[C:20](Cl)(=[O:22])[CH3:21].[K+].[Br-]>C(O)C>[C:20]([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]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[O:13])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 253877Potassium BromideHCID 183678643-Amino-6-chloro-2-(pyridine-2-carbonyl)indole

Product 1

HCID 183679943-Acetylamino-6-chloro-2-(pyridine-2-carbonyl)indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared according to the procedure described in Example 19 employing 3-amino-6-chloro-2-(pyridine-2-carbonyl)indole (Example 125) and acetyl chloride. m.p.: 211-212° C. (ethanol) 1H-NMR (DMSO-d6) δ: 12.02 (1H, br s), 10.34 (1H, br s), 8.82 (1H, d, J=4.4 Hz), 8.15-8.07 (2H, m), 7.85 (1H, d, J=8.8 Hz), 7.75-7.70 (1H, m), 7.63 (1H, d, J=1.8 Hz), 7.07 (1H, dd, J=1.8, 8.8 Hz), 2.02 (3H, s) IR (KBr) ν: 3450, 1690, 1620, 1580, 1570, 1480, 1350, 1240, 1180, 1160, 1030, 760 cm−1

Sources & evidence

ORD record
ord-da86509d4eea4172ad8bdc9e347573af
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

Loading…