Potassium Carbonate → HCID 59632933, compound

HRID 2369093Notes

Reaction equation

HRID 2369093 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:11]=[C:10]([C:20]([O:22][CH3:23])=[O:21])[CH:9]=2)=[N:6][CH:7]=1.[CH3:24][S:25]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)(=[O:27])=[O:26].C([O-])([O-])=O.[K+].[K+]>COCCOC.CCOC(C)=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[N:12]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([C:32]3[CH:31]=[CH:30][CH:29]=[C:28]([S:25]([CH3:24])(=[O:27])=[O:26])[CH:33]=3)=[CH:7][N:6]=2)=[CH:9][C:10]([C:20]([O:22][CH3:23])=[O:21])=[N:11]1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 59632248HCID 59632248, compound

Product 1

HCID 59632933HCID 59632933, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Methyl 5-(5-bromopyridin-2-yl)-1-(2-chlorophenyl)-1H-pyrazole-3-carboxylate (200 mg, 0.51 mmol), 3-(methylsulfonyl)phenylboronic acid (120 mg, 0.60 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (11) dichloromethane adduct (20 mg, 24 μmol), and K2CO3 (0.45 mL of a 3.5M aqueous solution, 1.6 mmol) were combined in DME (2.5 mL) in a microwave reaction vessel. The dark mixture was heated at 120° C. for 5 minutes. The reaction mixture was diluted with EtOAc and H2O. The aqueous layer was removed and extracted with additional EtOAc. The combined organics were dried over Na2SO4, treated with some decolorizing carbon and filtered through a pad of Celite. Concentration of the filtrates under reduced pressure and purification by flash column chromatography eluting with 0% to 50% MeCN/CH2Cl2 afforded methyl 1-(2-chlorophenyl)-5-(5-(3-(methylsulfonyl)phenyl)pyridin-2-yl)-1H-pyrazole-3-carboxylate as a pale yellow foam. This material was carried on to the subsequent step. MS(ES): 468 [M+H]+.

Workup

  1. customThe aqueous layer was removed
  2. extractionextracted with additional EtOAc
  3. dry with materialThe combined organics were dried over Na2SO4
  4. additiontreated with some decolorizing carbon
  5. filtrationfiltered through a pad of Celite
  6. customConcentration of the filtrates under reduced pressure and purification by flash column chromatography
  7. washeluting with 0% to 50% MeCN/CH2Cl2

Sources & evidence

ORD record
ord-76a2f60fb5214ddaad7c364b20e295fe
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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