5-Methoxyoxindole → HCID 178487101, compound

HRID 1615364Notes

Reaction equation

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

Participants

Reactant 2

HCID 15142865-Methoxyoxindole2×

HCID 178519313HCID 178519313, compound

Product 1

HCID 178487101HCID 178487101, compoundYield 53.2%

Procedure

The title compound (34 mg, 53%) was synthesized as a orange red solid according to the method described for Example A67 (oil temp 75° C., reflux 2 h) using 5-methoxylindolin-2-one (29 mg, 0.18 mmol) and 3-(pyridin-3-ylethynyl)-1H-indazole-6-carbaldehyde (40 mg, 0.163 mmol), followed by additional 90 min with additional 5-methoxylindolin-2-one (5.8 mg, 0.036 mmol). 1H NMR (400 MHz, DMSO-d6) δ 13.80 (s, br, 1H, NH), 10.46 (s, 1H, NH), 8.90 (s, 1H), 8.63 (d, J=4.4 Hz, 1H), 8.12 (dt, J=8.0 Hz, 1H), 8.04 (d, J=8.4 Hz, 1H), 7.98 (s, 1H), 7.79 (s, 1H), 7.58 (d, J=8.4 Hz, 1H), 7.52 (dd, J=8.0 Hz, J=4.8 Hz, 1H), 7.13 (d, J=1.6 Hz, 1H), 6.86 (dd, J=8.0 Hz, J=2.4 Hz, 1H), 6.80 (d, J=8.4 Hz, 1H), 3.59 (s, 3H); MS ESI 393.2 [M+H]+, calcd for [C24H16N4O2+H]+ 393.1.

Workup

customdescribed for Example A67 (oil temp 75° C., reflux 2 h)

Sources & evidence

ORD record: ord-cd4dbf71b56c4fe588014c4e0d25d745
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

Loading…