Cesium carbonate → methyl 6-(4-chloro-1H-pyrazol-1-yl)-5-methylnicotinate

HRID 715410Notes

Reaction equation

HRID 715410 reaction equation
F[C:2]1[C:11]([CH3:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[Cl:13][C:14]1[CH:15]=[N:16][NH:17][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[Cl:13][C:14]1[CH:15]=[N:16][N:17]([C:2]2[C:11]([CH3:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=2)[CH:18]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 275241H-Pyrazole, 4-chloro-HCID 53419770Methyl 6-fluoro-5-methylpyridine-3-carboxylate

Product 1

HCID 89874760methyl 6-(4-chloro-1H-pyrazol-1-yl)-5-methylnicotinateYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 6-fluoro-5-methylnicotinate (800 mg, 4.73 mmol, Step-1 of Amine-36), 4-chloro-1H-pyrazole (509 mg, 4.97 mmol), and cesium carbonate (3.08 g, 9.46 mmol) in DMF (16 mL) stirred at 60° C. for 1 hour. After cooling to rt, the mixture is diluted with EtOAc (150 mL) and washed with water (100 mL×3). The organic phase is filtered through silica gel, and the filtrate is concentrated to give 1.19 g (>99% yield) of the title compound as white solid.

Workup

  1. temperatureAfter cooling to rt
  2. washwashed with water (100 mL×3)
  3. filtrationThe organic phase is filtered through silica gel
  4. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-1fcebdf2c4944617856f6c8e6eaab143
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

Loading…