Potassium Carbonate → Methyl 4-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylate

HRID 1845404Notes

Reaction equation

HRID 1845404 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[S:5][CH:6]=1.C([O-])([O-])=O.[K+].[K+].CC1(C)COB([C:24]2[N:28]([CH3:29])[N:27]=[CH:26][CH:25]=2)OC1>O1CCOCC1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:29][N:28]1[C:24]([C:2]2[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[S:5][CH:6]=2)=[CH:25][CH:26]=[N:27]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12752071Methyl 4-bromothiophene-2-carboxylateHCID 441194445-(5,5-Dimethyl-1,3,2-dioxaborinan-2-YL)-1-methyl-1H-pyrazole

Product 1

HCID 57826540Methyl 4-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 4-bromo-2-thiophenecarboxylate (1 g, 4.52 mmol) in dioxane/H2O (5:1, 16 mL) was added K2CO3 (2.7 g, 19 mmol), bis(tri-t-butylphosphine)palladium(0) (116 mg, 0.226 mmol) and 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (1.2 g, 5.88 mmol). The reaction mixture was heated to 80° C. in a sealed tube. After 1 h, the reaction was partitioned between H2O-DCM and the aqueous phase was extracted several times with DCM. The combined organic fractions were dried over Na2SO4, concentrated and used directly: LCMS (ES) m/z 223 (M+H)+.

Workup

  1. customthe reaction was partitioned between H2O-DCM
  2. extractionthe aqueous phase was extracted several times with DCM
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cede866d168e4afeb61c41b3399977bc
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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