4-bromo-2,3-dihydro-1H-indol-2-one → HCID 178517037, compound

HRID 1615353Notes

Reaction equation

HRID 1615353 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:11])[NH:6]2.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH:21]=O)[CH:19]=2)[CH:14]=[N:13]1>>[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18](/[CH:21]=[C:4]3\[C:5](=[O:11])[NH:6][C:7]4[C:3]\3=[C:2]([Br:1])[CH:10]=[CH:9][CH:8]=4)[CH:19]=2)[CH:14]=[N:13]1

Participants

3

Reactant 2

HCID 27631904-bromo-2,3-dihydro-1H-indol-2-oneHCID 185383681H-Indazole-6-carbaldehyde

Product 1

HCID 178517037HCID 178517037, compoundYield 38.3%

Procedure

The title compound was synthesized according to the method of Example A19, utilizing 4-bromoindolin-2-one (50 mg, 0.23 mmol) and 1H-indazole-6-carbaldehyde (34.5 mg, 0.23 mmol). On completion the reaction mixture was stored at rt overnight. Filtration and rinsing with xs EtOH provided the title compound as an orange solid (30 mg, 38%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.36 (br. s., 1H), 10.91 (br. s., 1H), 8.78 (s, 1H), 8.73 (s, 1H), 8.13 (s, 1H), 7.80 (d, J=8.28 Hz, 1H), 7.65 (d, J=8.28 Hz, 1H), 7.22 (d, J=8.28 Hz, 1H), 7.16 (t, J=7.78 Hz, 1H), 6.88 (d, J=7.78 Hz, 1H); MS ESI [M+H]+ 340.1/341.9, calcd for [C16H10BrN3O+H]+ 340.0/342.0.

Workup

  1. customThe title compound was synthesized
  2. filtrationFiltration
  3. washrinsing with xs EtOH

Sources & evidence

ORD record
ord-3a0db05472104b46a192c36b0bf07d5e
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

Loading…