Pyrazole → HCID 58081197, compound

HRID 928373Notes

Reaction equation

HRID 928373 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14].[NH:15]1[CH:19]=[CH:18][CH:17]=[N:16]1.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C>[N:15]1([CH2:2][C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=2[O:13][CH3:14])[CH:19]=[CH:18][CH:17]=[N:16]1

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoate

Product 1

HCID 58081197HCID 58081197, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of methyl 4-(bromomethyl)-3-methoxybenzoate (400 mg, 1.544 mmol) and 1H-pyrazole (105 mg, 1.544 mmol) and K2CO3 (533 mg, 3.86 mmol) in DMF (5 ml) was stirred for 3.5 h at rt. A saturated solution of NaHCO3 was added and the mixture was extracted with ethyl acetate. The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to afford crude Methyl 4-((1H-pyrazol-1-yl)methyl)-3-methoxybenzoate. MS [M+H]+=247.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d94f48233c646469508e065cb17f0e5
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

Loading…