Potassium Carbonate → HCID 59489537, compound

HRID 1879177Notes

Reaction equation

HRID 1879177 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9](Br)=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2].[NH:13]1[C:17](B(O)O)=[CH:16][CH:15]=[N:14]1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:17]2[NH:13][N:14]=[CH:15][CH:16]=2)=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylateHCID 112519791H-Pyrazole-5-boronic acid

Product 1

HCID 59489537HCID 59489537, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid ethyl ester (2.0 g, 7.99 mmol) in toluene (60 mL), water (20 mL) and ethanol (20 mL) was added 1H-pyrazole-5-boronic acid (1.79 g, 15.99 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), and potassium carbonate (3.30 g, 23.98 mmol). The resulting mixture was degassed three times and heated to 100° C. for 16 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (200 mL) and washed with brine (2×100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by flash column chromatography (hexanes:ethyl acetate, 1:1) to provide 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid ethyl ester (1.5 g, 83% yield) as a yellow solid. MS (M+H)+=238; Rt=1.2 min.

Workup

  1. customThe resulting mixture was degassed three times
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additiondiluted with ethyl acetate (200 mL)
  4. washwashed with brine (2×100 mL)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (hexanes:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-9a6c6831134a473eba41b1314a1f4fe8
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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