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

HRID 2383569Notes

Reaction equation

HRID 2383569 reaction equation
N1[C:9]2[C:4](=[CH:5][C:6](/[CH:10]=[C:11]3/[C:12](=[O:20])[NH:13][C:14]4[C:19]/3=[CH:18][CH:17]=[CH:16][CH:15]=4)=[CH:7][CH:8]=2)C=N1.N1C2C(=CC=CC=2)CC1=O.[NH:31]1[C:39]2C(=CC=C(C=O)C=2)C=[N:32]1>>[NH:32]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6](/[CH:10]=[C:11]3/[C:12](=[O:20])[NH:13][C:14]4[C:19]/3=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:5]=2)[CH:39]=[N:31]1

Participants

4

Reactant 3

HCID 321710OxindoleHCID 185383681H-Indazole-6-carbaldehydeHCID 178517063HCID 178517063, compound

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 (E)-3-((1H-indazol-5-yl)methylene)indolin-2-one 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-5ec3e3de7af5448b8557d27e9a082d03
Source dataset
uspto-grants-2012_09
Patent number
US08263596B2

Reaction notes

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