4-Chloro-2-[(ethoxycarbonyl)amino]benzonitrile → 3-Amino-6-chloro-1-ethoxycarbonyl-2-(4-methylthiobenzoyl)indole

HRID 379747

Reaction equation

HRID 379747 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[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[S:19]>>[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:17]=1[C:18](=[S:19])[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 183678884-Chloro-2-[(ethoxycarbonyl)amino]benzonitrileHCID 183681522-Bromo-4'-methylthioacetophenone

Product 1

HCID 183678543-Amino-6-chloro-1-ethoxycarbonyl-2-(4-methylthiobenzoyl)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 2-bromo-4′-methylthioacetophenone (Cutler et al., J. Am. Chem. Soc., 1952, 74, 5475). 1H-NMR (CDCl3) δ: 8.25 (1H, d, J=1.8 Hz), 7.67 (2H, d, J=8.4 Hz), 7.53 (1H, d, J=8.4 Hz), 7.31-7.23 (3H, m), 5.75 (2H, br s), 3.82 (2H, q, J=7.0 Hz), 2.51 (3H, s), 0.89 (3H, t, J=7.0 Hz)

Sources & evidence

ORD record
ord-703604968bed48e4821efb5271421c29
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Linked notes

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