5-Methoxyoxindole → HCID 178487096, compound

HRID 1615362Notes

Reaction equation

[O:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2)[CH3:2].[CH:13]([C:15]1[CH:23]=[C:22]2[C:18]([C:19](/[CH:24]=[CH:25]/[C:26]3[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=3)=[N:20][NH:21]2)=[CH:17][CH:16]=1)=O>>[CH3:2][O:1][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])/[C:6]/2=[CH:13]/[C:15]1[CH:23]=[C:22]2[C:18]([C:19](/[CH:24]=[CH:25]/[C:26]3[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=3)=[N:20][NH:21]2)=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 15142865-Methoxyoxindole

HCID 86651992HCID 86651992, compound

Product 1

HCID 178487096HCID 178487096, compoundYield 23%

Procedure

The title compound (20 mg, 23%) was synthesized as an orange red solid according to the method described for Example A67 (oil temp 75° C., reflux 90 min) using 5-methoxylindolin-2-one (32.6 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 13.50 (s, 1H), 12.90 (s, br, 1H), 10.45 (s, 1H), 8.37 (d, J=8.4 Hz, 1H), 7.96 (d, J=8.0 Hz, 2H), 7.92 (s, 1H), 7.86 (d, J=8.0 Hz, 2H), 7.79 (s, 1H), 7.74 (d, J=16.8 Hz, 1H), 7.63 (d, J=16.4 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.19 (s, 1H), 6.86 (dd, J=8.8 Hz, J=2.4 Hz, 1H), 6.80 (d, J=8.4 Hz, 1H), 3.60 (s, 3H); MS ESI 438.2 [M+H]+, calcd for [C26H19N3O4+H]+ 438.1.

Workup

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

Sources & evidence

ORD record: ord-8fd27109239d444cac9866c83a6e4fc3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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