Hydrazine hydrate (1:1) → 6-chloro-4-(trifluoromethyl)-1H-pyrazolo[4,3-c]pyridin-3(2H)-one

HRID 588103Notes

Reaction equation

Cl[C:2]1[C:7]([C:8](OC)=[O:9])=[C:6]([C:12]([F:15])([F:14])[F:13])[N:5]=[C:4]([Cl:16])[CH:3]=1.O.[NH2:18][NH2:19]>CN(C=O)C>[Cl:16][C:4]1[N:5]=[C:6]([C:12]([F:15])([F:14])[F:13])[C:7]2[C:8](=[O:9])[NH:18][NH:19][C:2]=2[CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A solution of methyl 4,6-dichloro-2-(trifluoromethyl)nicotinate (535.9 mg, 1.956 mmol) in DMF (2 ml) was charged with hydrazine hydrate (190 μL, 3.92 mmol) and heated to 150° C. for 30 min under microwave irradiation. Concentrated in vacuo and washed residue with DCM. Purified via flash chromatography (0-20% MeOH/DCM) to provide 6-chloro-4-(trifluoromethyl)-1H-pyrazolo[4,3-c]pyridin-3(2H)-one MS: [M+H]+ m/z 238.

Workup

concentrationConcentrated in vacuo
washwashed residue with DCM
customPurified via flash chromatography (0-20% MeOH/DCM)

Sources & evidence

ORD record: ord-d21975efff9b45ca9a2145d53240a433
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

Loading…