Methanol → Ethyl 4-ethoxy-1-(4-fluorophenyl)pyrazole-3-carboxylate

HRID 1465184Notes

Reaction equation

HRID 1465184 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([OH:13])[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:26][CH3:27].CO>CN(C=O)C.C(Cl)Cl>[CH2:26]([O:13][C:11]1[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:9][N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:12]=1)[CH3:27]

Participants

7

Reactant 4

HCID 887MethanolHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 730292Ethyl 1-(4-fluorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylate

Product 1

HCID 66611816Ethyl 4-ethoxy-1-(4-fluorophenyl)pyrazole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of D1 (9.6 g, 38 mmol, 1.0 eq.) and K2CO3 (6.8 g, 50 mmol, 1.3 eq.) in dry DMF (100 mL) was added at RT iodoethane (4.0 mL, 7.8 g, 50 mmol, 1.3 eq.). After stirring for 72 h at RT the mixture was cooled to 0° C. MeOH (5 mL) was added, the mixture was diluted with DCM (200 mL) and washed with water and phosphate buffer. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give the product D2 as a brown solid which was used without further purification in the subsequent step. MS (ES) C14H15FN2O3 requires: 278. Found: 279 (M+H)+.

Workup

  1. temperaturewas cooled to 0° C
  2. washwashed with water and phosphate buffer
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57e6532bcfd64476957ad73a83a64889
Source dataset
uspto-grants-2015_04
Patent number
US08999982B2

Reaction notes

Loading…