Potassium Carbonate → HCID 22050346, compound

HRID 1867031Notes

Reaction equation

HRID 1867031 reaction equation
[Cl:1][C:2]1[C:3](=[O:18])[N:4]([C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])[C:5]([CH3:9])=[CH:6][C:7]=1[OH:8].C([O-])([O-])=O.[K+].[K+].[F:25][C:26]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:27]=1[CH2:28]Br>CC(N(C)C)=O.O>[Cl:1][C:2]1[C:3](=[O:18])[N:4]([C:10]2[C:11]([F:17])=[CH:12][CH:13]=[CH:14][C:15]=2[F:16])[C:5]([CH3:9])=[CH:6][C:7]=1[O:8][CH2:28][C:27]1[CH:30]=[CH:31][C:32]([F:34])=[CH:33][C:26]=1[F:25]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 547242093-chloro-1-(2,6-difluorophenyl)-4-hydroxy-6-methylpyridin-2(1H)-one

Product 1

HCID 22050346HCID 22050346, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 3-chloro-1-(2,6-difluorophenyl)-4-hydroxy-6-methylpyridin-2(1H)-one (0.27 g, 1.00 mmol) in DMA (5 mL) was added K2CO3 followed by the addition of 2,4-difluorobenzyl bromide (0.128 mL, 1 mmol). The reaction mixture stirred at room temperature for 2 hours and then was diluted in water. The reaction mixture was extracted with ethyl acetate, the organic extracts were dried over Na2SO4 and the filtrate was concentrated. The resulting residue was purified by flash column chromatography (ethyl acetate/hexane 3:4 v/v) to afford the desired product. 1H-NMR (CD3OD, 400 MHz) δ 7.60 (m, 2H), 7.25 (m, 2H), 7.04 (m, 2H), 6.71 (s, 1H), 5.36 (s, 2H), 2.11 (s, 3H); ES-HRMS m/z 398.0551 (M+H calculated for C19H13NO2F4Cl requires 398.0571).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic extracts were dried over Na2SO4
  3. concentrationthe filtrate was concentrated
  4. customThe resulting residue was purified by flash column chromatography (ethyl acetate/hexane 3:4 v/v)

Sources & evidence

ORD record
ord-1741c9bae26c46789039933c1da99b54
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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