Pyrazole → Methyl 1-cyclopentyl-6-oxo-5-(1H-pyrazol-1-yl)-1,6-dihydropyridine-3-carboxylate

HRID 253088Notes

Reaction equation

HRID 253088 reaction equation
Br[C:2]1[C:7](=[O:8])[N:6]([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[CH:3]=1.[NH:18]1[CH:22]=[CH:21][CH:20]=[N:19]1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[CH:9]1([N:6]2[C:7](=[O:8])[C:2]([N:18]3[CH:22]=[CH:21][CH:20]=[N:19]3)=[CH:3][C:4]([C:14]([O:16][CH3:17])=[O:15])=[CH:5]2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 15946267Methyl 5-bromo-1-cyclopentyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 66845814Methyl 1-cyclopentyl-6-oxo-5-(1H-pyrazol-1-yl)-1,6-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 5-bromo-1-cyclopentyl-6-oxo-1,6-dihydropyridine-3-carboxylate (300 mg, 1.00 mmol), pyrazole (23 mg, 0.34 mmol), K2CO3 (99 mg, 0.72 mmol), CuI (9.1 mg, 0.048 mmol), N1—N2-dimethylethane-1,2-diamine (5 uL, 0.048 mmol) in toluene (3 mL) was heated to 100° C. for 17 h. The mixture was brought to RT and quenched with saturated NH4Cl, brine, dried over MgSO4 and chromatographed on silica gel using 3:1 hexanes:ethylacetate to afford the title compound as a white solid. MS m/z: 288 (M+1).

Workup

  1. customwas brought to RT
  2. customquenched with saturated NH4Cl, brine
  3. dry with materialdried over MgSO4
  4. customchromatographed on silica gel using 3:1 hexanes

Sources & evidence

ORD record
ord-e47a89dfa19141ab86f86c1b466293ca
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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