Ethyl Bromide → 5-Bromo-3-(1-ethyl-5-methyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-one

HRID 407663Notes

Reaction equation

HRID 407663 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.Br[CH2:18][CH3:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:15]=[C:14]([CH3:16])[N:13]([CH2:18][CH3:19])[N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 580441425-Bromo-1-methyl-3-(5-methyl-1H-pyrazol-3-ylamino)pyridin-2(1H)-one

Product 1

HCID 580442355-Bromo-3-(1-ethyl-5-methyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-oneYield 48.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A 100-mL round-bottomed flask was charged with 118a (800 mg, 2.83 mmol), bromoethane (216 mg, 1.98 mmol), K2CO3 (780 mg, 5.66 mmol), and DMF (20 mL). The mixture was heated at 85° C. overnight. It was then filtered and the filtrate was evaporated in vacuo. The residue was purified by silica-gel column chromatography eluting with 1:20 methanol/dichloromethane to afford 118b as a red solid (298 mg, 37%). MS-ESI: [M+H]+ 311.0. 1H NMR (500 MHz, DMSO-d6) δ 8.28 (s, 1H), 7.99 (d, J=2.5 Hz, 1H), 7.35 (d, J=2.5 Hz, 1H), 5.85 (s, 1H), 3.98-3.94 (m, 2H), 3.48 (s, 3H), 2.19 (s, 3H), 1.27 (t, J=7.0 Hz, 3H).

Workup

  1. filtrationIt was then filtered
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by silica-gel column chromatography
  4. washeluting with 1:20 methanol/dichloromethane

Sources & evidence

ORD record
ord-c3fc166932ab40889bebf22e0d2ffb8f
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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