Potassium Carbonate → HCID 57899213, compound

HRID 549422Notes

Reaction equation

HRID 549422 reaction equation
[CH3:1][O:2][C:3](=[O:17])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([C@H:12]2[CH2:16][CH2:15][CH2:14][NH:13]2)=[CH:8][CH:7]=1.Br[CH2:19][CH2:20][C:21]1[C:22]([CH3:27])=[N:23][NH:24][C:25]=1[CH3:26].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:19][CH2:20][C:21]2[C:22]([CH3:27])=[N:23][NH:24][C:25]=2[CH3:26])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5728794-(2-Bromoethyl)-3,5-dimethyl-1H-pyrazoleHCID 57899267HCID 57899267, compound

Product 1

HCID 57899213HCID 57899213, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

(E)-3-((R)-4-Pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester (697 mg, 3 mmol) and 4-(2-bromo-ethyl)-3,5-dimethyl-1H-pyrazole (734 mg, 3.62 mmol) were dissolved in acetonitrile, potassium carbonate (833 mg, 6 mmol) was added, and the reaction mixture heated under nitrogen at 85° C. for 14 h. Cooled to room temperature, diluted with DCM (20 mL) and filtered through a plug of celite. Wash plug with DCM (30 mL). Filtrate was concentrated to 110 mL and columned on silica with EtOAc/hexane. Product elutes with neat EtOAc, and after concentrating gave (E)-3-(4-{(R)-1-[2-(3,5-dimethyl-1H-pyrazol-4-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester as a tacky, pale yellow solid (804 mg, 2.275 mmol, 75%).

Workup

  1. temperatureCooled to room temperature
  2. filtrationfiltered through a plug of celite
  3. concentrationFiltrate was concentrated to 110 mL
  4. concentrationafter concentrating

Sources & evidence

ORD record
ord-cf661c6bd36b41c583a8f45bf40133cd
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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