Oxindole → HCID 178517050, compound

HRID 1615361Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH:11]([C:13]1[CH:21]=[C:20]2[C:16]([C:17](/[CH:22]=[CH:23]/[C:24]3[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=3)=[N:18][NH:19]2)=[CH:15][CH:14]=1)=O>>[O:10]=[C:2]1[NH:1][C:9]2[C:4](/[C:3]/1=[CH:11]\[C:13]1[CH:21]=[C:20]3[C:16]([C:17](/[CH:22]=[CH:23]/[C:24]4[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=4)=[N:18][NH:19]3)=[CH:15][CH:14]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

Reactant 2

HCID 321710Oxindole

HCID 86651992HCID 86651992, compound

Product 1

HCID 178517050HCID 178517050, compoundYield 21%

Procedure

The title compound (17 mg, 21%) was synthesized as an orange solid according to the method described for Example A67 (oil temp 75° C., reflux 90 min) using indolin-2-one (26.6 mg, 0.2 mmol) and (E)-4-(2-(6-formyl-1H-indazol-3-yl)vinyl)benzoic acid (58.4 mg, 0.2 mmol). 1H NMR (400 MHz, DMSO-d6) δ 13.49 (s, 1H), 12.90 (s, br, 1H), 10.64 (s, 1H), 8.37 (d, J=8.4 Hz, 1H), 7.97 (d, J=8.4 Hz, 2H), 7.91 (s, 1H), 7.86 (d, J=8.0 Hz, 2H), 7.80 (s, 1H), 7.74 (d, J=16.8 Hz, 1H), 7.63 (d, J=15.6 Hz, 1H partially overlapping with the singlet at 7.62), 7.62 (s, 1H partially overlapping with the doublet at 7.63), 7.24 (t, J=7.4 Hz, 1H), 6.91-6.82 (m, 2H); MS ESI 408.2 [M+H]+, calcd for [C25H17N3O3+H]+ 408.1.

Workup

customdescribed for Example A67 (oil temp 75° C., reflux 90 min)

Sources & evidence

ORD record: ord-44758956d94444eaaa62c83f509e9be6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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