Cesium carbonate → 5-Bromo-1-methyl-3-(5-methyl-1-(oxetan-3-yl)-1H-pyrazol-3-ylamino)pyridin-2(1H)-one

HRID 593119Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:15]=[C:14]([CH3:16])[NH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.I[CH:18]1[CH2:21][O:20][CH2:19]1.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:15]=[C:14]([CH3:16])[N:13]([CH:18]3[CH2:21][O:20][CH2:19]3)[N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-bromo-1-methyl-3-(5-methyl-1H-pyrazol-3-ylamino)pyridin-2(1H)-one 115a (200 mg, 0.71 mmol), 3-iodooxetane (647 mg, 3.53 mmol), Cs2CO3 (1150 mg, 3.53 mmol), and acetonitrile (5 mL) was heated at 80° C. in a sealed tube overnight. The mixture was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 20:1 dichloromethane/methanol to afford the 312a as a yellow solid (120 mg, 50%). MS-ESI: [M+H]+ 339.1

Workup

temperatureThe mixture was then cooled to room temperature
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by silica-gel column chromatography
washeluting with 20:1 dichloromethane/methanol

Sources & evidence

ORD record: ord-cc63b70bc9af417ba148f2930258afb2
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238655B2

Reaction notes

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