5-Methoxyoxindole → HCID 178487100, compound

HRID 1615332Notes

Reaction equation

HRID 1615332 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15](/[CH:19]=[CH: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>>[CH3:1][O:2][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](/[CH:20]=[CH: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

3

Reactant 2

HCID 15142865-MethoxyoxindoleHCID 86651944(E)-3-(2-(pyridin-3-yl)vinyl)-1H-indazole-6-carbaldehyde

Product 1

HCID 178487100HCID 178487100, compoundYield 67.2%

Procedure

The title compound (53 mg, 67%) was synthesized as an orange red solid according to the method described for Example A67 (oil temp 75° C., reflux 90 min) using 5-methyoxyoxindole (32.6 mg, 0.2 mmol) and (E)-3-(2-(pyridin-3-yl)vinyl)-1H-indazole-6-carbaldehyde (49.8 mg, 0.2 mmol). 1H NMR indicated 4:1 mixture of E/Z isomers. 1H NMR (400 MHz, DMSO-d6) δ 13.50 (br. s, 1H, NH), 10.44 (s, 1H, NH), 8.91 (d, 1H), 8.48 (d, J=4.8 Hz, 1H), 8.36 (d, J=8.4 Hz, 1H), 8.20 (d, J=7.6 Hz, 1H), 7.92 (s, 1H), 7.79 (s, 1H), 7.73 (d, J=16.8 Hz, 1H), 7.59 (d, J=16.4 Hz, 1H), 7.54 (d, J=8.8 Hz, 1H), 7.43 (dd, J=8.0 Hz, 5.2 Hz, 1H), 7.19 (d, 1H), 6.86 (dd, J=8.4 Hz, 2.0 Hz, 1H), 6.81 (d, J=8.4 Hz, 1H), 3.78 (s, 3H); MS ESI 395.2 [M+H]+, calcd for [C24H18N4O2+H]+ 395.1.

Workup

  1. customdescribed for Example A67 (oil temp 75° C., reflux 90 min)
  2. addition4:1 mixture of E/Z isomers

Sources & evidence

ORD record
ord-dd55799c77a149309837dbcd127dcc08
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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