5-(Bromoacetyl)-3-phenylisoxazole → 3-Amino-6-chloro-1-(ethoxycarbonyl)-2-(3-phenyl-5-isoxazoyl)indole

HRID 379775Notes

Reaction equation

HRID 379775 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[O:24][N:23]=[C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=1)=[O: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]([C:20]1[O:24][N:23]=[C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=1)=[O:19]

Participants

3

Reactant 2

HCID 27355325-(Bromoacetyl)-3-phenylisoxazoleHCID 183678884-Chloro-2-[(ethoxycarbonyl)amino]benzonitrile

Product 1

HCID 701137053-Amino-6-chloro-1-(ethoxycarbonyl)-2-(3-phenyl-5-isoxazoyl)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 5-(bromoacetyl)-3-phenylisoxazole. 1H-NMR (CDCl3) δ: 8.27 (1H, d, J=1.8 Hz), 7.89-7.84 (2H, m), 7.56-7.47 (5H, m), 7.30 (1H, dd, J=1.8, 8.4 Hz), 6.18 (2H, s), 4.13 (2H, q, J=7.2 Hz), 1.10 (3H, t, J=7.2 Hz)

Sources & evidence

ORD record
ord-42ff006a9f674e6f91ef89708afb01f2
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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