Potassium Carbonate → HCID 21035357, compound

HRID 1867155Notes

Reaction equation

HRID 1867155 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[CH2:14]Br)[CH3:2].[Br:17][C:18]1[C:19](=[O:34])[N:20]([C:26]2[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=2[F:33])[C:21]([CH3:25])=[CH:22][C:23]=1[OH:24].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[CH2:14][O:24][C:23]1[CH:22]=[C:21]([CH3:25])[N:20]([C:26]2[C:27]([F:33])=[CH:28][CH:29]=[CH:30][C:31]=2[F:32])[C:19](=[O:34])[C:18]=1[Br:17])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21035356HCID 21035356, compoundHCID 54724178HCID 54724178, compound

Product 1

HCID 21035357HCID 21035357, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl[2-(bromomethyl)-5-fluorophenoxy]acetate (from Step 2) (0.59 g, 2.03 mmol) and 3-bromo-1-(2,6-difluorophenyl)-4-hydroxy-6-methylpyridin-2(1H)-one (0.61 g, 1.93 mmol) in DMF (3.0 mL) was added K2CO3 (0.34 g, 2.43 mmol). After 2 h at RT, DMF was removed by distillation. The crude product was washed with 5% citric acid, extracted in DCM, dried over Na2SO4, filtered, and concentrated onto silica gel. Purified by flash column chromatography using 50% EtOAc/hexane as the eluent. Obtained product as a pale yellow solid (0.45 g, 42%). 1H NMR (CD3OD/400 MHz) δ7.21 (q, 3H, J=8.4 Hz), 6.80 (m, 2H), 6.69 (s, 1H), 6.15 (s, 1H), 5.40 (s, 2H), 4.84 (s, 2H), 4.23 (q, 2H, J=6.8 Hz), 2.08 (s, 3H), 1.26 (t, 3H, J=6.8 Hz). ESHRMS m/z 526.0446 and 528.0414 (M+H calculated for C23H20BrF3NO5 requires 526.0471 and 528.0454).

Workup

  1. customDMF was removed by distillation
  2. washThe crude product was washed with 5% citric acid
  3. extractionextracted in DCM
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated onto silica gel
  7. customPurified by flash column chromatography

Sources & evidence

ORD record
ord-d392bb03a8884a09ab3a76509f50f342
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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