5-Bromoisatin → 5-bromo-1-(diphenylmethyl)-1H-indole-2,3-dione

HRID 2385100Notes

Reaction equation

HRID 2385100 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].O1C2=CC3C(=O)C(=O)NC=3C=C2OCC1.Br[CH:29]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.BrCC1OC(C(F)(F)F)=CC=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:29]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:6](=[O:11])[C:5]2=[O:12]

Participants

5

Reactant 4

HCID 68895-BromoisatinHCID 236603BromodiphenylmethaneHCID 20298022,3-dihydro-6H-[1,4]dioxino[2,3-f]indole-7,8-dioneHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furan

Product 1

HCID 673566275-bromo-1-(diphenylmethyl)-1H-indole-2,3-dione

Procedure

Following the procedure as described in PREPARATION 26A and making non-critical variations using 5-bromoisatin to replace 2,3-dihydro-6H-[1,4]dioxino[2,3-f]indole-7,8-dione, and bromodiphenylmethane to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, 5-bromo-1-(diphenylmethyl)-1H-indole-2,3-dione was obtained (76%): 1H NMR (300 MHz, CDCl3) δ 7.74-7.67 (m, 1H), 7.46-7.20 (m, 11H), 6.96 (s, 1H), 6.37 (d, J=8.5 Hz, 1H).

Sources & evidence

ORD record
ord-fb17e51816f147768fac4d88cf6d72a0
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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