5-Methoxyoxindole → HCID 178471184, compound

HRID 1615328Notes

Reaction equation

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

Participants

Reactant 2

HCID 15142865-Methoxyoxindole

HCID 86651946HCID 86651946, compound

Product 1

HCID 178471184HCID 178471184, compoundYield 77%

Procedure

The title compound (60 mg, 77%) was synthesized as an orange red solid according to the method described for Example A67 (oil temp 75° C., reflux 2 h) using 5-methoxyoxindole (26.8 mg, 0.2 mmol) and (E)-ethyl 3-(6-formyl-1H-indazol-3-yl)acrylate (48.8 mg, 0.2 mmol). 1H NMR (400 MHz, DMSO-d6) δ 13.80 (brs, 1H, NH), 10.44 (s, 1H, NH), 8.26 (d, J=8.4 Hz, 1H), 7.96 (s, 1H), 7.92 (d, J=16.4 Hz, 1H), 7.77 (s, 1H), 7.56 (d, J=8.4 Hz, 1H), 7.14 (d, 1H), 6.90-6.80 (m, 3H), 4.23 (q, J=7.2 Hz, 2H), 3.58 (s, 3H), 2.29 (t, J=7.2 Hz, 3H); MS ESI 390.3 [M+H]+, calcd for [C22H19N3O4+H]+ 390.1.

Workup

customdescribed for Example A67 (oil temp 75° C., reflux 2 h)

Sources & evidence

ORD record: ord-58067f24ed554c33a8e230d7d4ed92f6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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