3-Bromophenol → 4-bromo-1-(diphenylmethyl)-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydro-2H-indol-2-one

HRID 1965356Notes

Reaction equation

HRID 1965356 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.BrC1C=C(O)C=CC=1.[Br:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[C:23](=[O:44])[C:24](=[O:43])[N:25]2[CH:30]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.FC(F)(F)C1OC(CN2C3C(=CC=CC=3)C(=O)C2=O)=CC=1>>[Br:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[C:23]([OH:44])([C:8]1[C:9]([OH:11])=[CH:10][C:5]3[O:4][CH2:3][CH2:2][O:1][C:6]=3[CH:7]=1)[C:24](=[O:43])[N:25]2[CH:30]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 4

HCID 115633-BromophenolHCID 91152732,3-Dihydro-1,4-benzodioxin-6-olHCID 673564881-((5-(Trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dioneHCID 673574234-Bromo-1-benzhydrylindoline-2,3-dione

Product 1

HCID 673766264-bromo-1-(diphenylmethyl)-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 2A and making non-critical variations using 2,3-dihydro-1,4-benzodioxin-6-ol to replace 3-bromophenol, and 4-bromo-1-benzhydrylindoline-2,3-dione to replace 1-((5-(trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dione, 4-bromo-1-(diphenylmethyl)-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydro-2H-indol-2-one was obtained (99%) as a colorless solid: 1H NMR (300 MHz, DMSO-d6) δ9.06 (s, 1H), 7.44-7.28 (m, 10H), 6.98-6.82 (m, 2H), 6.68 (s, 1H), 6.33 (d, J=7.4 Hz, 1H), 6.16 (s, 1H), 4.23-4.08 (m, 4H); MS (ES+) m/z 566.1 (M+23), 568.1 (M+23).

Sources & evidence

ORD record
ord-beca2a2c7775476aafb672181704a162
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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