Water → HCID 22049965, compound

HRID 1867112Notes

Reaction equation

HRID 1867112 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N:12]1[C:17]([CH3:18])=[CH:16][C:15]([OH:19])=[CH:14][C:13]1=[O:20])[C:5]([O:7][CH3:8])=[O:6].[F:21][C:22]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:23]=1[CH2:24]Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.C(#N)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N:12]1[C:17]([CH3:18])=[CH:16][C:15]([O:19][CH2:24][C:23]2[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:22]=2[F:21])=[CH:14][C:13]1=[O:20])[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 54724176HCID 54724176, compound

Product 1

HCID 22049965HCID 22049965, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Methyl 3-chloro-4-(4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)benzoate (from Step 1) (2.4 g, 8.17 mmol) was taken up in DMF (10 ml). 2,4-difluorobenzylbromide (1.05 ml, 8.17 mmol) and K2CO3 (1.13 g, 8.17 mmol) were added. The reaction stirred for 6 hours at room temperature. At this time, the reaction was poured into water (200 ml) and extracted with ethyl acetate. The ethyl acetate layer was dried over Na2SO4, filtered, and the solvent removed in vacuo to give amber oil (2.62 g, 77% crude yield). LC/MS, tr=2.79 minutes (5 to 95% acetonitrile/water over 5 minutes at 1 ml/min with detection 254 nm, at 50° C.). ES-MS m/z 294 (M+H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customto give amber oil (2.62 g, 77% crude yield)

Sources & evidence

ORD record
ord-b3c1d7f0928a48a4b61acc7fb174c4d6
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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