HCID 19372784, compound → HCID 19372799, compound

HRID 129231Notes

Reaction equation

HRID 129231 reaction equation
[CH3:1][Mg]Br.[F:4][C:5]([F:41])([F:40])[C:6]([NH:8][CH:9]1[CH2:38][C:13]2=[CH:14][N:15]([S:20]([C:23]3[C:28]([CH:29]([CH3:31])[CH3:30])=[CH:27][C:26]([CH:32]([CH3:34])[CH3:33])=[CH:25][C:24]=3[CH:35]([CH3:37])[CH3:36])(=[O:22])=[O:21])[C:16]3[CH:17]=[CH:18][CH:19]=[C:11]([C:12]=32)[C:10]1=[O:39])=[O:7]>C1COCC1>[OH:39][C:10]1([CH3:1])[C:11]2[C:12]3[C:13](=[CH:14][N:15]([S:20]([C:23]4[C:24]([CH:35]([CH3:37])[CH3:36])=[CH:25][C:26]([CH:32]([CH3:33])[CH3:34])=[CH:27][C:28]=4[CH:29]([CH3:30])[CH3:31])(=[O:21])=[O:22])[C:16]=3[CH:17]=[CH:18][CH:19]=2)[CH2:38][CH:9]1[NH:8][C:6](=[O:7])[C:5]([F:4])([F:40])[F:41]

Participants

4

Reactant 2

HCID 19372784HCID 19372784, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 19372799HCID 19372799, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl magnesium bromide (1M THF solution 8 equivalents) was allowed to react with a solution of 3,4-dihydro-4-trifluoroacetylamino-1-(2,4,6-triisopropylphenylsulfonyl)-5H-benz[cd]indol-5-one (1.5 g, 1.43 mmol) in THF (14.3 ml). The reaction mixture was processed in a conventional manner. The residue was subjected to silica gel column chromatography, eluting with n-hexane-ethyl acetate (4:1) to afford 1.3 g (84%) of the title compound as an amorphous crystalline product.

Workup

  1. washeluting with n-hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-9451f257b02044ed8b39c5c0206c9584
Source dataset
uspto-grants-1995_11
Patent number
US05466689

Reaction notes

Loading…