5,6-Dimethoxyindolin-2-one → HCID 178486512, compound

HRID 1615357Notes

Reaction equation

HRID 1615357 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7](=[O:14])[CH2:6]2.[N:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]2[C:31]3[C:26](=[CH:27][C:28]([CH:32]=O)=[CH:29][CH:30]=3)[NH:25][N:24]=2)=[CH:17][CH:16]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7](=[O:14])/[C:6]/2=[CH:32]/[C:28]1[CH:27]=[C:26]2[C:31]([C:23](/[CH:22]=[CH:21]/[C:18]3[CH:17]=[CH:16][N:15]=[CH:20][CH:19]=3)=[N:24][NH:25]2)=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 2229935,6-Dimethoxyindolin-2-oneHCID 86651943HCID 86651943, compound

Product 1

HCID 178486512HCID 178486512, compoundYield 42.4%

Procedure

The title compound (36 mg, 42%) was synthesized as an orange red solid according to the method described for Example A67 (oil temp 75° C., reflux 90 min) using 5,6-dimethoxyindolin-2-one (38.6 mg, 0.2 mmol) and (E)-3-(2-(pyridin-4-yl)vinyl)-1H-indazole-6-carbaldehyde (49.8 mg, 0.2 mmol). 1H NMR (400 MHz, DMSO-d6) δ 13.54 (s, 1H), 10.39 (s, 1H), 8.60-8.53 (m, 2H), 8.35 (d, J=7.2 Hz, 1H), 7.94 (s, 1H), 7.87 (d, J=16.4 Hz, 1H), 7.75-7.67 (m, 2H), 7.63-7.50 (m, 3H), 7.25 (s, 1H), 6.53 (s, 1H), 3.80 (s, 3H), 3.55 (s, 3H); MS ESI 425.2 [M+H]+, calcd for [C25H20N4O3+H]+ 425.1.

Workup

  1. customdescribed for Example A67 (oil temp 75° C., reflux 90 min)

Sources & evidence

ORD record
ord-b00ff602f9994209976afd7ac9daab5e
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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