Potassium Carbonate → HCID 67501824, compound

HRID 1187764Notes

Reaction equation

HRID 1187764 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=3)=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 66705807HCID 66705807, compound

Product 1

HCID 67501824HCID 67501824, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

In a pressure tube, (S)-4-[2-(4-amino-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (100 mg), 2-chloro-5-(trifluoromethyl)pyridine (57 mg) and potassium carbonate (431 mg) were combined with toluene (1 ml) to give a yellow solution. The mixture was degassed by bubbling through argon for several minutes. BINAP (12 mg) and palladium(II)acetate (2 mg) were then added and the tube was sealed. The reaction mixture was stirred at 110° C. for 1 hour. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was purified by flash chromatography (SiO2; gradient: 0% to 40% EtOAc in hexane) to afford (S)-2,2-dimethyl-4-{2-[4-(5-trifluoromethyl-pyridin-2-ylamino)-phenyl]-ethyl}-oxazolidine-3-carboxylic acid tert-butyl ester (55 mg, 38%) as a yellow amorphous solid. MS (ISP): 466.3 ([M+H]+), 410.2 ([M+H—C4H8]+), 366.2 ([M+H—C4H8—CO2]+).

Workup

  1. customto give a yellow solution
  2. customThe mixture was degassed
  3. customby bubbling through argon for several minutes
  4. additionBINAP (12 mg) and palladium(II)acetate (2 mg) were then added
  5. customthe tube was sealed
  6. temperatureThe reaction mixture was then cooled to room temperature
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (SiO2; gradient: 0% to 40% EtOAc in hexane)

Sources & evidence

ORD record
ord-f3965a339bfd4d24b6e5504bfa7d510b
Source dataset
uspto-grants-2014_03
Patent number
US08673950B2

Reaction notes

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