Chloro-N,N-dimethylformiminium chloride → N-((5-bromo-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)methylene)-N-methylmethanaminium chloride

HRID 1475955Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[CH:10]=[C:4]2[CH:3]=1.[Cl-].[Cl:20][CH:21]=[N+:22]([CH3:24])[CH3:23]>ClCCCl>[Cl-:20].[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)[C:10]([CH:21]=[N+:22]([CH3:24])[CH3:23])=[C:4]2[CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a stirred suspension of 5-bromo-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine (200 mg, 0.66 mmol) in 1,2-dichloroethane (6 mL) was added N-(Chloromethylene)-N-methylmethanaminium chloride (195 mg, 1.5 mmol). The mixture was stirred at 20° C. for 20 h then heated to 50° C. for 1 h at which time monitoring the reaction by LC indicated all starting material had converted to the title compound. The solids were collected by filtration and dried under reduced pressure to afford the title compound as a solid (260 mg, 100%). LCMS m/z 331.0, 333.0 (M-(CH3)2NH+H2O)+, ret. time=2.13 min.

Workup

temperaturethen heated to 50° C. for 1 h at which time
customthe reaction by LC

Sources & evidence

ORD record: ord-59fef1b24fe744e0b39ad8de87cd9c44
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018395B2

Reaction notes

Loading…