6-Pyridin-3-yl-1,3-dihydro-indol-2-one → HCID 178516992, compound

HRID 1615238Notes

Reaction equation

HRID 1615238 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][C:12](=[O:16])[NH:13]3)=[CH:9][CH:8]=2)[CH:2]=1.[NH:17]1[C:21]2[CH:22]=[CH:23][C:24]([CH:26]=O)=[CH:25][C:20]=2[N:19]=[N:18]1>>[NH:17]1[C:21]2[CH:22]=[CH:23][C:24](/[CH:26]=[C:11]3/[C:12](=[O:16])[NH:13][C:14]4[C:10]/3=[CH:9][CH:8]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:15]=4)=[CH:25][C:20]=2[N:19]=[N:18]1

Participants

3

Reactant 2

HCID 219155796-Pyridin-3-yl-1,3-dihydro-indol-2-oneHCID 178519382HCID 178519382, compound

Product 1

HCID 178516992HCID 178516992, compound

Procedure

According to the method of Example A19, utilizing 6-(pyridin-3-yl)indolin-2-one (37.1 mg, 0.18 mmol) and 1H-benzo[d][1,2,3]triazole-5-carbaldehyde (25.8 mg, 0.18 mmol), the title compound was obtained as an orange solid (20 mg, 34%). 1H NMR (400 MHz, DMSO-d6) δ ppm 15.96 (br.s. 1H),10.83 (s, 1H), 8.86 (br. s., 1H), 8.57-8.61 (m, 1H), 8.45 (br. s., 0.5H), 8.18 (br. s., 1H), 8.05 (d, J=7.83 Hz, 1H), 7.95 (br. s., 1H), 7.86 (s, 0.5H), 7.75 (br. s., 1H), 7.64 (d, J=7.33 Hz, 1H), 7.49 (dd, J=7.71, 4.93 Hz, 1H), 7.22 (d, J=7.58 Hz, 1H), 7.17 (s, 1H); 1H NMR (400 MHz, DMF-d7) δ ppm 10.77 (br. s., 1H), 8.94 (br. s., 1H), 8.61-8.65 (m, 1H), 8.42 (s, 1H), 8.13 (t, J=7.96 Hz, 1H), 7.93 (s, 1H), 7.90 (d, J=8.84 Hz, 1H), 7.78 (d, J=7.83 Hz, 1H), 7.52 (dd, J=7.71, 4.67 Hz, 1H), 7.33 (s, 1H), 7.30 (d, J=7.83 Hz, 1H); MS ESI 340.1 (100) [M+H]+, calcd for [C20H13N5O+H]+340.4.

Sources & evidence

ORD record
ord-4b8c55fd7665453a8d055e6cbcaddc0d
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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