5-Chlorooxindole → HCID 178517159, compound

HRID 1615296Notes

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.[Cl:29]C1C=C2C(=CC=1)NC(=O)C2>>[Cl: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

Reactant 2

HCID 1528015-Chlorooxindole

HCID 178517054HCID 178517054, compound

Product 1

HCID 178517159HCID 178517159, compound

Procedure

According to the procedure for the synthesis of (E)-3-((3-((E)-2-(pyridin-4-yl)vinyl)-1H-indazol-6-yl)methylene)indolin-2-one (Example A57), except substituting 5-chlorooxindole (14 mg, 0.08 mmol), the title compound was prepared as an orange solid (13.5 mg, 42%). 1H NMR (400 MHz, d6-DMSO) δ 13.63 (br s, 1H), 10.78 (br. s, 1H), 8.56 (d, J=4.0 Hz, 2H), 8.40 (d, J=10.0 Hz, 1H), 7.91 (s, 1H), 7.89 (d, J=13.2 Hz, 2H), 7.72 (d, J=3.5 Hz, 2H), 7.57 (d, J=12.0 Hz, 1H), 7.52 (d, J=12.0 Hz, 2H), 7.30 (d, J=10.0 Hz, 1H), 6.90 (d, J=11.5 Hz, 1H); MS ESI 399.2 [M+H]+, calcd for [C23H15ClN4O+H]+ 399.09.

Sources & evidence

ORD record: ord-cb61d114c02540afab33a5208e7646a2
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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