Potassium Carbonate → HCID 57742969, compound

HRID 1801975Notes

Reaction equation

HRID 1801975 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]([N:8]([C:10]1[C:19]([F:20])=[C:18]([F:21])[CH:17]=[CH:16][C:11]=1[C:12]([O:14]C)=O)[CH3:9])=[O:7])[CH3:2].FC1C(NC)=C(C=CC=1F)C(OC)=O.C(=O)([O-])[O-].[K+].[K+].ClC(=O)CC(OCC)=O>C1COCC1.O>[F:21][C:18]1[C:19]([F:20])=[C:10]2[C:11]([C:12]([OH:14])=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:22])[C:6](=[O:7])[N:8]2[CH3:9])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 67406911HCID 67406911, compoundHCID 67408030HCID 67408030, compound

Product 1

HCID 57742969HCID 57742969, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
24 °C

Procedure

Methyl 2-(3-ethoxy-N-methyl-3-oxopropanamido)-3,4-difluorobenzoate. At 0° C., a suspension of methyl 3,4-difluoro-2-(methylamino)benzoate (1.10 g, 5.47 mmol) and potassium carbonate (0.98 g, 7.1 mmol) in THF (10 mL) was treated dropwise with ethyl 3-chloro-3-oxopropanoate (0.90 mL, 7.11 mmol). The mixture was warmed to 24° C., stirred for 3 hours, diluted with water, and extracted with EtOAc. The combined organic layers were dried over MgSO4, and evaporated. Purification by flash chromatography (EtOAc/hexanes) gave the title compound. MS (ESI) m/z: Calculated; 315.3: Observed; 316.1. 1H NMR (300 MHz, CDCl3) δ ppm 7.81-7.91 (1H, m), 7.28-7.37 (1H, m), 4.12 (2H, q, J=7.1 Hz), 3.92 (3H, s), 3.23 (3H, s), 3.10 (2H, s), 1.23 (3H, t, J=7.2 Hz).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customevaporated
  4. customPurification by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-6701988ff5284435b6846b36841d6745
Source dataset
uspto-grants-2013_01
Patent number
US08349868B2

Reaction notes

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