Benzyl Bromide → 1-Benzyl-3-(3,5-dimethyl-phenyl)-3-hydroxy-1,3-dihydro-indol-2-one

HRID 1297762Notes

Reaction equation

HRID 1297762 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:18])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C.[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(#N)C>[CH2:38]([N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=2)([OH:19])[C:10]1=[O:18])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 5297657Indol-2-one, 3-(3,5-dimethylphenyl)-3-hydroxy-1,3-dihydro-

Product 1

HCID 589146821-Benzyl-3-(3,5-dimethyl-phenyl)-3-hydroxy-1,3-dihydro-indol-2-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using a method similar to Preparation 17 with 3-(3,5-dimethyl-phenyl)-3-hydroxy-1,3-dihydro-indol-2-one (50 mg, 0.20 mmol), 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine (0.065 ml, 0.22 mmol) and benzyl bromide (0.024 mL, 0.20 mmol) in acetonitrile (1 mL) gives 68 mg (100%) of the title compound which was used without further purification.

Sources & evidence

ORD record
ord-319b71a10c524443937d5093b63515c3
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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