Isatin → 1-(diphenylmethyl)-5-methyl-1H-indole-2,3-dione

HRID 425544Notes

Reaction equation

HRID 425544 reaction equation
N1C2C(=CC=CC=2)C(=O)C1=O.[CH3:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[C:16]2=[O:23].BrCCC1CC1.Br[CH:31]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[C:32]1([CH:31]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:18]2[C:19]3[C:15](=[CH:14][C:13]([CH3:12])=[CH:21][CH:20]=3)[C:16](=[O:23])[C:17]2=[O:22])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 4

HCID 7054IsatinHCID 118405-MethylisatinHCID 236603BromodiphenylmethaneHCID 22636989(2-Bromoethyl)cyclopropane

Product 1

HCID 666426781-(diphenylmethyl)-5-methyl-1H-indole-2,3-dione

Procedure

Following the procedure as described in PREPARATION 2A, and making non-critical variations to replace isatin with 5-methylisatin, and (2-bromoethyl)cyclopropane with 1,1′-(bromomethylene)dibenzene, the title compound was obtained (74%) as a bright orange solid: 1H NMR (300 MHz, CDCl3) δ 7.42-7.26 (m, 11H), 7.09 (d, 1H), 6.95 (s, 1H), 6.37 (d, 1H), 2.24 (s, 3H).

Sources & evidence

ORD record
ord-a395496f2d4a4a459af74af53d28849b
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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