Oxindole → (3E)-3-(1H-indazol-6-ylmethylidene)-1H-indol-2-one

HRID 1615221Notes

Reaction equation

HRID 1615221 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].[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH:20]=O)[CH:18]=2)[CH:13]=[N:12]1>>[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17](/[CH:20]=[C:3]3/[C:2](=[O:10])[NH:1][C:9]4[C:4]/3=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:18]=2)[CH:13]=[N:12]1

Participants

3

Reactant 2

HCID 321710OxindoleHCID 185383681H-Indazole-6-carbaldehyde

Product 1

HCID 178517060(3E)-3-(1H-indazol-6-ylmethylidene)-1H-indol-2-one

Procedure

The title compound was synthesized according to the method described for Example A1 except reacting oxindole (67 mg, 0.216 mmol) with 1H-indazole-6-carbaldehyde (73 mg, 0.238 mmol) to obtain 32 mg, 51%. 1H NMR (400 MHz, CD3OD) δ 8.14 (s, 1H), 7.91 (d, J=8.5 Hz, 1H), 7.89 (s, 2H), 7.65 (d, J=7.6 Hz, 1H), 7.47 (d, J=8.4 Hz, 1H), 7.25 (t, J=7.7 Hz, 1H), 6.93 (d, J=7.8 Hz, 1H), 6.87 (t, J=7.6 Hz, 1H); MS ESI 262.0 [M+H]+, calcd for [C16H11N3O+H]+ 262.10.

Workup

  1. customto obtain 32 mg, 51%

Sources & evidence

ORD record
ord-d2be69af9afd42e28d553619a218a76f
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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