5,6-Dimethoxyindolin-2-one → HCID 178486513, compound

HRID 1615355Notes

Reaction equation

HRID 1615355 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.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH:24]=O)[CH:22]=2)[CH:17]=[N:16]1>>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21](/[CH:24]=[C:6]3/[C:7](=[O:14])[NH:8][C:9]4[C:5]/3=[CH:4][C:3]([O:2][CH3:1])=[C:11]([O:12][CH3:13])[CH:10]=4)[CH:22]=2)[CH:17]=[N:16]1

Participants

3

Reactant 2

HCID 2229935,6-Dimethoxyindolin-2-oneHCID 185383681H-Indazole-6-carbaldehyde

Product 1

HCID 178486513HCID 178486513, compoundYield 67%

Procedure

The title compound (43 mg, 67%) was synthesized as an orange yellow 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 1H-indazole-6-carbaldehyde (29.2 mg, 0.2 mmol). 1H NMR (400 MHz, DMSO-d6) δ 13.26 (s, 1H), 10.36 (s, 1H), 8.14 (s, 1H), 7.95-7.85 (m, 2H), 7.57 (s, 1H), 7.46-7.37 (m, 1H), 7.24 (s, 1H), 6.52 (s, 1H), 3.78 (s, 3H), 3.53 (s, 3H); MS ESI 322.1 [M+H]+, calcd for [C18H15N3O3+H]+ 322.1.

Workup

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

Sources & evidence

ORD record
ord-e02449d308c648e7b4c751a9fe0a0735
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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