Oxindole → HCID 178497725, compound

HRID 1615360Notes

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:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[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:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[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 71818810HCID 71818810, compound

Product 1

HCID 178497725HCID 178497725, compoundYield 83%

Procedure

The title compound (40 mg, 83%) was synthesized as an orange solid according to the method described for Example A67 (oil temp 75° C., reflux 150 min) using indolin-2-one (26.6 mg, 0.2 mmol) and (E)-methyl 4-(2-(6-formyl-1H-indazol-3-yl)vinyl)benzoate (61.2 mg, 0.2 mmol). 1H NMR (400 MHz, DMSO-d6) δ 13.60 (s, 1H), 10.70 (s, 1H), 9.00 (s, 1H), 8.29 (d, J=8.0 Hz, 1H), 8.08 (d, J=8.4 Hz, 1H), 8.00 (s, 1H), 7.98 (d, J=8.0 Hz, 2H), 7.88 (d, J=8.0 Hz, 2H), 7.77 (d, J=8.4 Hz, 1H, partially overlapping with the doublet at 7.74), 7.74 (d, J=17.2 Hz, 1H, partially overlapping with the doublet at 7.77), 7.63 (d, J=17.2 Hz, 1H), 7.23 (t, J=7.6 Hz, 1H), 7.01 (t, J=7.6 Hz, 1H), 6.84 (d, J=7.6 Hz, 1H), 3.86 (s, 3H); MS ESI 422.3 [M+H]+, calcd for [C26H19N3O3+H]+ 422.1.

Workup

customdescribed for Example A67 (oil temp 75° C., reflux 150 min)

Sources & evidence

ORD record: ord-da8f3724826e44c1a6861141057f90c6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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