HCID 86651967, compound → HCID 178517046, compound

HRID 1615305Notes

Reaction equation

HRID 1615305 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[C:11]3/[C:12](=[O:20])[NH:13][C:14]4[C:19]/3=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:8]=2)[CH:3]=[N:2]1.[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[C:23](C2C3C(=CC(C=O)=CC=3)NN=2)[CH:22]=1>>[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[C:23]([C:3]2[C:4]3[C:9](=[CH:8][C:7]([CH:10]=[C:11]4[C:19]5[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=5)[NH:13][C:12]4=[O:20])=[CH:6][CH:5]=3)[NH:1][N:2]=2)[CH:22]=1

Participants

3

Reactant 2

HCID 86651967HCID 86651967, compoundHCID 178517060(3E)-3-(1H-indazol-6-ylmethylidene)-1H-indol-2-one

Product 1

HCID 178517046HCID 178517046, compound

Procedure

According to the procedure for the synthesis of (E)-3-((1H-indazol-6-yl)methylene)-indolin-2-one, except substituting 3-(quinolin-3-yl)-1H-indazole-6-carbaldehyde (8 mg, 0.03 mol), the title compound was obtained as a yellow solid (4.3 mg, 38%). A mixture of (E)- and (Z)-isomers (94:6 by NMR) was obtained. 1H NMR (400 MHz, d6-DMSO) δ 13.75 (br s, 1H), 10.66 (br. s, 1H), 9.61 (d, J=2.0 Hz, 1H), 9.04 (d, J=2.3 Hz, 1H), 8.47 (d, J=8.8 Hz, 1H), 8.22 (d, J=7.8 Hz, 1H), 8.08 (d, J=8.0 Hz, 1H), 8.01 (s, 1H), 7.83 (s, 1H), 7.80 (td, J=6.8, 1.3 Hz, 1H), 7.68 (t, J=7.8, 1H), 7.64 (d, J=7.8 Hz, 1H), 7.61 (d, J=7.8 Hz, 1H), 7.25 (t, J=7.8 Hz, 1H), 6.90 (d, J=8.3 Hz, 1H), 6.86 (t, J=7.8 Hz, 1H); MS ESI 389.1 [M+H]+, calcd for [C25H16N4O+H]+ 389.13.

Sources & evidence

ORD record
ord-c63fed2b6357434985c62181190be9ef
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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