Potassium Carbonate → HCID 22051176, compound

HRID 1832024Notes

Reaction equation

HRID 1832024 reaction equation
[Br:1][C:2]1[C:3](=[O:14])[N:4]([CH2:10][CH:11]2[CH2:13][CH2:12]2)[C:5]([CH3:9])=[CH:6][C:7]=1[OH:8].C([O-])([O-])=O.[K+].[K+].[F:21][C:22]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:23]=1[CH2:24]Br>CC(N(C)C)=O.O>[Br:1][C:2]1[C:3](=[O:14])[N:4]([CH2:10][CH:11]2[CH2:12][CH2:13]2)[C:5]([CH3:9])=[CH:6][C:7]=1[O:8][CH2:24][C:23]1[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:22]=1[F:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 54724190HCID 54724190, compound

Product 1

HCID 22051176HCID 22051176, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a mixture of 3-bromo-1-(cyclopropylmethyl)-4-hydroxy-6-methylpyridin-2(1H)-one (0.276 g, 1.07 mmol) and K2CO3 (0.148 g, 1.07 mmol) in DMA (4 mL) was added 2,4-difluorobenzyl bromide (0.14 ml, 1.07 mmol). The mixture stirred at room temperature for 1.5 hours. The reaction mixture was diluted in water and extracted with ethyl acetate. The organic extracts were dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography (ethyl acetate/hexane 1:1 v/v). The appropriate fractions were combined, and concentrated. 1H-NMR (CD3OD, 400 MHz) δ 7.60 (q, 1H), 7.04 (m, 2H), 6.42 (s, 1H), 5.26 (s, 2H), 4.06 (s, 1H), 4.04 (s, 1H), 2.50 (s, 3H), 0.53 (m, 2H), 0.43 (m, 2H); ES-HRMS m/z 384.0392 (M+H calculated for C17H17N2OBrF2 requires 384.0405).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography (ethyl acetate/hexane 1:1 v/v)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f6e3877026d343809d173b233169b199
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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