Potassium Carbonate → HCID 22050346, compound

HRID 1832021Notes

Reaction equation

HRID 1832021 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-74b08cea281a42d58dd21a556f45c297
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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