Sodium hydride → HCID 117942102, compound

HRID 1499119Notes

Reaction equation

HRID 1499119 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.[H-].[Na+].Cl[C:10]1[N:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]>CN(C=O)C>[CH3:20][C:18]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([N:4]2[CH:5]=[CH:6][C:2]([CH3:1])=[N:3]2)[N:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 13055804Methyl 2-chloro-6-methylpyridine-3-carboxylateHCID 178428694HCID 178428694, compound

Product 1

HCID 117942102HCID 117942102, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-methyl-1H-pyrazole (1.1 g, 13.4 mmol) in DMF (5 ml) was added sodium hydride (1.0 g, 60% in oil) at 0° C. The reaction mixture was stirred for 1 h at 0° C. and then. A solution of methyl 2-chloro-6-methylnicotinate (4.3 g, 23.16 mmol) in DMF (5 mL) was added dropwise to the reaction mixture at 0° C. After addition, the mixture was heated to 80° C. and stirred for 12 h. After this time, the mixture was poured into ice-water and extracted and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo and then purified by normal phase silica gel column (EtOAc/hepate) to provide methyl 6-methyl-2-(3-methyl-1H-pyrazol-1-yl)nicotinate as a brown semi-solid.

Workup

  1. additionAfter addition
  2. temperaturethe mixture was heated to 80° C.
  3. stirringstirred for 12 h
  4. extractionextracted
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. custompurified by normal phase silica gel column (EtOAc/hepate)

Sources & evidence

ORD record
ord-5f15fe8b6bdc4a5f872bd6d8f6cec4dc
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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