2-Chloropyridine → HCID 70664638, compound

HRID 1854532Notes

Reaction equation

HRID 1854532 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([NH2:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=1)=[O:5])C.Cl[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[OH-].[Na+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCO>[C:12]1([N:8]2[C:9]([NH:11][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:10][C:6]([C:4]([OH:3])=[O:5])=[N:7]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

9

Reactant 5

HCID 79772-ChloropyridineHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23630921Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate

Product 1

HCID 70664638HCID 70664638, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

200 mg (0.865 mmol) of 5-Amino-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester were dissolved in 5 ml DMF and 108 mg (0.95 mmol, 1.1 eq) of 2-Chloropyridine, 620 mg (1.9 mmol, 2.2 eq) of Cs2CO3, 20 mg (0.1 eq) of palladium(II)acetate and 60 mg of xantphos (0.12 eq) were added and the resulting mixture heated to 100° C. for 6 hours. The mixture was filtered over a pad of Celite and 2 ml of 1N NaOH (2 mmol, 2.3 eq) were added together with 2 ml of EtOH. After stirring overnight at RT the crude reaction mixture was subjected to HPLC chromatography delivering 60 mg of product. (Yield: 25%)

Workup

  1. customreaction mixture

Sources & evidence

ORD record
ord-0db0575ee1c145efb435df318c71dc8c
Source dataset
uspto-grants-2015_02
Patent number
US08962671B2

Reaction notes

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