4-Chloro-2-[(ethoxycarbonyl)amino]benzonitrile → 3-Amino-6-chloro-1-(ethoxycarbonyl)-2-(4-methylpyridine-2-carbonyl)indole
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:26]=[C:25]([CH3:27])[CH:24]=[CH:23][N:22]=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]([C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][N:22]=1)=[O:20]Participants
3
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 2-(bromoacetyl)-4-methylpyridine hydrobromide (F. H. Case et al., J. Am. Chem. Soc., 1956, 78, 5842). 1H-NMR (CDCl3) δ: 8.46 (1H, d, J=4.8 Hz), 8.22 (1H, d, J=1.8 Hz), 7.89 (1H, s), 7.51 (1H, d, J=8.4 Hz), 7.24 (1H, dd, J=1.8, 8.4 Hz), 7.20 (1H, br d, J=4.8 Hz), 5.97 (2H, br s), 3.80 (2H, q, J=7.0 Hz), 2.46 (3H, s), 0.90 (3H, t, J=7.0 Hz)
Sources & evidence
- ORD record
- ord-fece09450da640518ff6a8cd745ee194
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06300363B1
Reaction notes
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