5-Bromo-2-oxindole → HCID 178517023, compound

HRID 1615219Notes

Reaction equation

HRID 1615219 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[NH:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH:21]=O)=[CH:20][C:15]=2[N:14]=[N:13]1>>[NH:12]1[C:16]2[CH:17]=[CH:18][C:19](/[CH:21]=[C:5]3/[C:6](=[O:11])[NH:7][C:8]4[C:4]/3=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=4)=[CH:20][C:15]=2[N:14]=[N:13]1

Participants

3

Reactant 2

HCID 6111935-Bromo-2-oxindoleHCID 178519382HCID 178519382, compound

Product 1

HCID 178517023HCID 178517023, compound

Procedure

The title compound was synthesized according to the method described for Example A1, except reacting 5-bromooxindole (39 mg, 0.185 mmol) with 1H-benzo[d][1,2,3]triazole-5-carbaldehyde (30 mg, 0.204 mmol) to obtain 32 mg, 51%. 1H NMR (400 MHz, d6-DMSO) δ 15.97 (s, 1H), 10.85 (s, 1H), 9.27 (s, 1H), 8.37 (d, J=9.2 Hz, 1H), 8.16 (s, 1H), 8.02 (s, 1H), 7.95 (d, J=8.4 Hz, 1H), 7.39 (d, J=8.2 Hz, 1H), 6.80 (d, J=8.3 Hz, 1H); MS ESI 341.0 [M+H]+, calcd for [C15H9BrN4O+H]+ 341.00.

Workup

  1. customto obtain 32 mg, 51%

Sources & evidence

ORD record
ord-810aa6b470374b51a0ab258cc0971d47
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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