Oxindole → HCID 178525373, compound

HRID 1615287Notes

Reaction equation

HRID 1615287 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]([OH:26])=[O:25])=[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]([OH:26])=[O:25])=[N:18][NH:19]3)=[CH:15][CH:14]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

3

Reactant 2

HCID 321710OxindoleHCID 86651960(E)-3-(6-formyl-1H-indazol-3-yl)acrylic acid

Product 1

HCID 178525373HCID 178525373, compoundYield 21.1%

Procedure

The title compound (7 mg, 21%) was synthesized as an orange solid according to the method described for Example A67 using oxindole (13.3 mg, 0.1 mmol) and (E)-3-(6-formyl-1H-indazol-3-yl)acrylic acid (21.6 mg, 0.1 mmol). NMR (400 MHz, DMSO-d6) δ 13.80 (br. s, 1H, NH), 10.64 (s, 1H, CO2H), 8.20 (d, J=8.4 Hz, 1H), 7.94 (s, 1H), 7.85 (d, J=16.4 Hz, 1H), 7.78 (s, 1H), 7.58-7.53 (m, 2H), 7.24 (t, J=7.6 Hz, 1H), 6.88 (d, J=8.0 Hz, 1H), 6.84 (t, J=7.8 Hz, 1H), 6.75 (d, J=16.0 Hz, 1H); MS ESI 332.1 [M+H]+, calcd for [C19H13N3O3+H]+ 322.1.

Sources & evidence

ORD record
ord-d54b8a902314480c93150642cfccd533
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

Loading…