Bromodiphenylmethane → 1-(diphenylmethyl)-4,6-dimethoxy-1H-indole-2,3-dione

HRID 1965403Notes

Reaction equation

HRID 1965403 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]2[C:4]=1[C:5](=[O:15])[C:6](=[O:14])[NH:7]2.O1C2=CC3C(=O)C(=O)NC=3C=C2OCC1.Br[CH:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.BrCC1OC(C(F)(F)F)=CC=1>>[C:33]1([CH:32]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[N:7]2[C:8]3[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=3)[C:5](=[O:15])[C:6]2=[O:14])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 4

HCID 236603BromodiphenylmethaneHCID 20298022,3-dihydro-6H-[1,4]dioxino[2,3-f]indole-7,8-dioneHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 115575224,6-dimethoxy-2,3-dihydro-1H-indole-2,3-dione

Product 1

HCID 673570521-(diphenylmethyl)-4,6-dimethoxy-1H-indole-2,3-dione

Procedure

Following the procedure as described in PREPARATION 26A and making non-critical variations using 4,6-dimethoxy-1H-indole-2,3-dione 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, 1-(diphenylmethyl)-4,6-dimethoxy-1H-indole-2,3-dione was obtained (90%): 1H NMR (300 MHz, DMSO-d6) δ7.49-7.19 (m, 10H), 6.72 (s, 1H), 6.21 (d, J=1.5 Hz, 1H), 5.87 (d, J=1.5 Hz, 1H), 3.86 (s, 3H), 3.70 (s, 3H).

Sources & evidence

ORD record
ord-1bcb0233d72f431fa02ebf387e73d9b1
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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