3-Bromophenol → 1-(diphenylmethyl)-3-hydroxy-3-(5-hydroxy-2,1,3-benzoxadiazol-4-yl)-1,3-dihydro-2H-indol-2-one

HRID 1407529Notes

Reaction equation

HRID 1407529 reaction equation
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=12.BrC1C=C(O)C=CC=1.[C:19]1([CH:25]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28](=[O:35])[C:27]2=[O:36])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.FC(F)(F)C1OC(CN2C3C(=CC=CC=3)C(=O)C2=O)=CC=1>>[C:37]1([CH:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]([OH:35])([C:9]3[C:4]4[C:5](=[N:1][O:2][N:3]=4)[CH:6]=[CH:7][C:8]=3[OH:10])[C:27]2=[O:36])[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

5

Reactant 4

HCID 115633-BromophenolHCID 19692771-(diphenylmethyl)-1H-indole-2,3-dioneHCID 673564881-((5-(Trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dioneHCID 1354568365-Hydroxybenzofurazan

Product 1

HCID 1363483471-(diphenylmethyl)-3-hydroxy-3-(5-hydroxy-2,1,3-benzoxadiazol-4-yl)-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 2A and making non-critical variations using 2,1,3-benzoxadiazol-5-ol to replace 3-bromophenol, and 1-(diphenylmethyl)-1H-indole-2,3-dione to replace 1-((5-(trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dione, 1-(diphenylmethyl)-3-hydroxy-3-(5-hydroxy-2,1,3-benzoxadiazol-4-yl)-1,3-dihydro-2H-indol-2-one was obtained (71%) as a colorless solid: MS (ES+) m/z 472.0 (M+23).

Sources & evidence

ORD record
ord-d7dd713933c843f09cef1bb396f7f7e0
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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