3-(2-Bromoacetyl)pyridine hydrobromide → 3-Amino-6-chloro-1-ethoxycarbonyl-2-(nicotinoyl)indole

HRID 379764Notes

Reaction equation

HRID 379764 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([NH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:3]=1.Br.Br[CH2:18][C:19]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)=[O:20]>>[NH2:7][C:6]1[C:5]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:9][CH:8]=2)[N:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:18]=1[C:19](=[O:20])[C:21]1[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=1

Participants

3

Reactant 2

HCID 27762343-(2-Bromoacetyl)pyridine hydrobromideHCID 183678884-Chloro-2-[(ethoxycarbonyl)amino]benzonitrile

Product 1

HCID 183677873-Amino-6-chloro-1-ethoxycarbonyl-2-(nicotinoyl)indole

Procedure

The title compound was prepared according to the procedure described in step 2 of Example 1 from 4-chloro-2-(ethoxycarbonylamino)benzonitrile (Example 1, step 1) and 3-(bromoacetyl)pyridine hydrobromide (H. McKennis et al., J. Org. Chem., 1963, 387). 1H-NMR (CDCl3) δ: 8.95 (1H, dd, J=0.7, 2.2 Hz), 8.70 (1H, dd, J=1.8, 4.8 Hz), 8.23 (1H, d, J=1.5 Hz), 8.03-7.99 (1H, m), 7.57 (1H, d, J=8.4 Hz), 7.41-7.28 (2H, m), 6.08 (2H, br s), 3.87 (2H, q, J=7.0 Hz), 0.92 (3H, t, J=7.0 Hz)

Sources & evidence

ORD record
ord-974a29c1eb4d42749018eb54d7eda627
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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