Propionyl chloride → 6-Chloro-2-(4-chloropyridine-2-carbonyl)-3-(propionylamino)indole

HRID 379865Notes

Reaction equation

HRID 379865 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]=[C:18]([Cl:20])[CH:17]=[CH:16][N:15]=1)=[O:13].[C:21](Cl)(=[O:24])[CH2:22][CH3:23]>>[Cl:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([NH:1][C:21](=[O:24])[CH2:22][CH3:23])=[C:3]([C:12]([C:14]3[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][N:15]=3)=[O:13])[NH:4]2)=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 62324Propionyl chlorideHCID 183681263-Amino-6-chloro-2-(4-chloropyridine-2-carbonyl)indole

Product 1

HCID 183681916-Chloro-2-(4-chloropyridine-2-carbonyl)-3-(propionylamino)indole

Procedure

The title compound was prepared according to the procedure described in Example 19 from 3-amino-6-chloro-2-(4-chloropyridine-2-carbonyl)indole (Example 68) and propionyl chloride. m.p.: 188-190° C. (recrystallized from ethyl acetate) 1H-NMR (CDCl3) δ: 11.68 (1 H, br s), 10.88 (1 H, br s), 8.70 (1 H, d, J=5.4 Hz), 8.54 (1 H, d, J=9.1 Hz), 8.37 (1 H, d, J=2.0 Hz), 7.58 (1 H, dd, J=2.1, 5.3 Hz), 7.40 (1 H, d, J=2.0 Hz), 7.06 (1 H, dd, J=1.1, 9.1 Hz), 2.63 (2 H, q, J=7.6 Hz), 1.37 (3 H, t, J=7.6 Hz).

Workup

  1. customm.p.: 188-190° C. (recrystallized from ethyl acetate) 1H-NMR (CDCl3) δ: 11.68 (1 H, br s), 10.88 (1 H, br s), 8.70 (1 H, d, J=5.4 Hz), 8.54 (1 H, d, J=9.1 Hz), 8.37 (1 H, d, J=2.0 Hz), 7.58 (1 H, dd, J=2.1, 5.3 Hz), 7.40 (1 H, d, J=2.0 Hz), 7.06 (1 H, dd, J=1.1, 9.1 Hz), 2.63 (2 H, q, J=7.6 Hz), 1.37 (3 H, t, J=7.6 Hz)

Sources & evidence

ORD record
ord-95088a1f8b234a5fb11a9bab41e4befc
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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