HCID 23092684, compound → HCID 67427594, compound

HRID 2235420Notes

Reaction equation

[CH:1]([CH:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:24]([O-])=O)=[C:10]([NH:13][C:14](=O)[C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:11]=2)[N:6]([CH3:27])[C:5]1=[O:28])([CH3:3])[CH3:2]>[Ni]>[CH:1]([CH:4]1[C:12]2[CH:11]=[C:10]3[NH:13][C:14]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=4)=[N:24][C:9]3=[CH:8][C:7]=2[N:6]([CH3:27])[C:5]1=[O:28])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

(rac)-7-Isopropyl-2-(4-methoxy-phenyl)-5-methyl-5,7-dihydro-1H-imidazo [4,5-f]indol-6-one is prepared from (rac)-N-(3-Isopropyl-1-methyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-4-methoxy-benzamide (443 mg) by hydrogenation at 70° C. as described in Example 1b) using Raney-nickel (70 mg). The catalyst is filtered off and the filtrate heated at 100° C. for 1 h. After a typical aqueous work-up the crude material is purified by flash chromatography on silica gel eluting with light petroleum/EtOAc (3:1) to give the desired compound (311 mg).

Workup

filtrationThe catalyst is filtered off
customAfter a typical aqueous work-up the crude material is purified by flash chromatography on silica gel eluting with light petroleum/EtOAc (3:1)

Sources & evidence

ORD record: ord-6037c8cc1044436497070c0e03f6e7b7
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714010B2

Reaction notes

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