5-Chlorooxindole → HCID 178517158, compound

HRID 1615304Notes

Reaction equation

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

Participants

Reactant 2

HCID 1528015-Chlorooxindole

HCID 178517044HCID 178517044, compound

Product 1

HCID 178517158HCID 178517158, compound

Procedure

According to the procedure for the synthesis of 3-((3-(pyridin-3-yl)-1H-indazol-6-yl)methylene)indolin-2-one, except substituting 5-chlorooxindole (5.3 mg, 0.031 mmol) the title compound was prepared as a yellow solid (6.5 mg, 54%). A mixture of (E)- and (Z)-isomers (68:32 by NMR) was obtained. 1H NMR (400 MHz, d6-DMSO) δ 13.77 (br s, 1H), 10.80 (br s, 1H), 9.24 (d, J=1.5 Hz, 1H), 8.63 (dd, J=4.8, 1.8 Hz, 1H), 8.41 (dt, J=7.8, 1.8 Hz, 1H), 8.28 (d, J=8.5 Hz, 1H), 8.21-8.16 (m, 1H), 7.98 (s, 1H), 7.89 (s, 1H), 7.57 (t, J=4.5, 1H), 7.55-7.52 (m, 1H), 7.31 (dd, J=8.3, 2.3 Hz, 1H), 6.91 (d, J=8.3 Hz, 1H); MS ESI 373.1 [M+H]+, calcd for [C21H13ClN4O+H]+ 373.08.

Sources & evidence

ORD record: ord-83dcea2c4adc4e0b9625af0454b95f2a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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