Potassium Carbonate → HCID 57672257, compound

HRID 252063Notes

Reaction equation

HRID 252063 reaction equation
CO[C:3](=[O:14])[C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Br:11])=[CH:6][C:5]=1[CH2:12]Br.[F:15][C:16]1([F:24])[CH2:21][CH2:20][CH:19]([CH2:22][NH2:23])[CH2:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[Br:11][C:7]1[CH:6]=[C:5]2[C:4](=[C:9]([Cl:10])[CH:8]=1)[C:3](=[O:14])[N:23]([CH2:22][CH:19]1[CH2:20][CH2:21][C:16]([F:24])([F:15])[CH2:17][CH2:18]1)[CH2:12]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15604494(4,4-Difluorocyclohexyl)methanamineHCID 59512234Methyl 4-bromo-2-(bromomethyl)-6-chlorobenzoate

Product 1

HCID 57672257HCID 57672257, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Bromo-2-bromomethyl-6-chlorobenzoic acid methyl ester (3.5 g, 9.35 mmol), (4,4-difluorocyclohexyl)methylamine (1.7 g, 11.39 mmol) and K2CO3 (3.15 g, 22.78 mmol) were stirred in toluene (10 mL) at 95° C. for 12 hours. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over anhydrous Na2—SO4. The solvent was removed under reduced pressure and the product was purified by column chromatography (10-25% EtOAc/Hexanes) to afford the title compound as a yellow foam (2.2 g, 45%), 1H NMR (300 MHz, CDCl3): 7.58 (s, 1H), 7.50 (s, 1H), 4.36 (s, 2H), 3.48 (d, 2H), 2.10-2.14 (m, 2H), 1.64-1.82 (m, 5H), 1.35-1.447 (m, 2H)

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2—SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe product was purified by column chromatography (10-25% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-0f01a18d2971497cb8d08f6f3d31908a
Source dataset
uspto-grants-2011_01
Patent number
US07868008B2

Reaction notes

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