5-Methylindolin-2-one → HCID 178422515, compound

HRID 1615297Notes

Reaction equation

HRID 1615297 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[C:17]3[C:12](=[CH:13][C:14](/[CH:18]=[C:19]4/[C:20](=[O:28])[NH:21][C:22]5[C:27]/4=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:15][CH:16]=3)[NH:11][N:10]=2)=[CH:3][CH:2]=1.[CH3:29]C1C=C2C(=CC=1)NC(=O)C2>>[CH3:29][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:28])/[C:19]/2=[CH:18]/[C:14]1[CH:13]=[C:12]2[C:17]([C:9](/[CH:8]=[CH:7]/[C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[N:10][NH:11]2)=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 53257165-Methylindolin-2-oneHCID 178517054HCID 178517054, compound

Product 1

HCID 178422515HCID 178422515, compoundYield 26%

Procedure

According to procedure for the synthesis of (E)-3-((3-((E)-2-(pyridin-4-yl)vinyl)-1H-indazol-6-yl)methylene)indolin-2-one, except substituting 5-methyloxindole (9 mg, 0.06 mmol) to give the title compound as an orange solid (5.9 mg, 26%). 1H NMR (400 MHz, d6-DMSO) δ 13.58 (br s, 1H), 10.53 (br s, 1H), 8.57 (br s, 2H), 8.36 (d, J=8.0 Hz, 1H), 7.93-7.46 (m, 8H), 7.06 (d, J=8.0 Hz, 1H), 6.79 (d, J=5.8 Hz, 1H), 2.16 (s, 3H); MS ESI 379.2 [M+H]+, calcd for [C24H18N4O+H]+ 379.15.

Sources & evidence

ORD record
ord-2dea99e512414e56b3e5faf532fa6c11
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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