1H-Indazole-5-carboxaldehyde → HCID 178516991, compound

HRID 1615239Notes

Reaction equation

HRID 1615239 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:25]2[C:20](=[CH:21][C:22]([CH:26]=O)=[CH:23][CH:24]=2)[CH:19]=[N:18]1>>[NH:17]1[C:25]2[C:20](=[CH:21][C:22](/[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:23][CH:24]=2)[CH:19]=[N:18]1

Participants

3

Reactant 2

HCID 212506441H-Indazole-5-carboxaldehydeHCID 219155796-Pyridin-3-yl-1,3-dihydro-indol-2-one

Product 1

HCID 178516991HCID 178516991, compound

Procedure

According to the method of Example A19, utilizing 6-(pyridin-3-yl)indolin-2-one (25 mg, 0.12 mmol) and 1H-indazole-5-carbaldehyde (17.4 mg, 0.12 mmol), the title compound was obtained as an orange solid (7 mg, 17%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.32 (br. s., 1H), 10.81 (s, 1H), 9.04 (s, 1H), 8.89 (d, J=1.26 Hz, 1H), 8.57 (dd, J=4.55, 1.26 Hz, 1H), 8.52 (d, J=7.83 Hz, 1H), 8.25 (s, 1H), 8.06-8.11 (m, 1H), 8.04 (s, 1H), 7.87 (d, J=7.83 Hz, 1H), 7.62 (d, J=8.84 Hz, 1H), 7.49 (dd, J=7.33, 4.55 Hz, 1H), 7.38 (dd, J=7.83, 1.26 Hz, 1H), 7.11 (d, J=1.01 Hz, 1H); MS ESI 339.1 (100) [M+H]+, calcd for [C21H14N4O+H]+ 339.4.

Sources & evidence

ORD record
ord-c3ab442d09324dffbba96adfda3a693b
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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