(2E)-3-(3-Nitrophenyl)acryloyl chloride → 2-[(E)-2-(3-amino-phenyl)-vinyl]-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

HRID 2235407Notes

Reaction equation

HRID 2235407 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[N:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:6](=[O:19])[C:5]2([CH3:21])[CH3:20].[N+:22]([C:25]1[CH:26]=[C:27](/[CH:31]=[CH:32]/[C:33](Cl)=O)[CH:28]=[CH:29][CH:30]=1)([O-])=O>>[NH2:22][C:25]1[CH:26]=[C:27](/[CH:31]=[CH:32]/[C:33]2[NH:1][C:2]3=[CH:3][C:4]4[C:5]([CH3:21])([CH3:20])[C:6](=[O:19])[N:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:8]=4[CH:9]=[C:10]3[N:11]=2)[CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 11063737(2E)-3-(3-Nitrophenyl)acryloyl chlorideHCID 178027445-Amino-3,3-dimethyl-6-nitro-1-pentyl-1,3-dihydro-indol-2-one

Product 1

HCID 674266922-[(E)-2-(3-amino-phenyl)-vinyl]-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-oneYield 52.9%

Procedure

2-[(E)-2-(3-Amino-phenyl)-vinyl]-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (177 mg) is prepared from A8 (251 mg) and (E)-3-(3-nitro-phenyl)-acryloyl chloride (200 mg; 1.01 mmol) as described in Example 28a and b.

Sources & evidence

ORD record
ord-7d87ab299c724f638f2e2cbe1eac1e32
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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