Potassium Carbonate → HCID 24955764, compound

HRID 1879175Notes

Reaction equation

HRID 1879175 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14](Br)=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]1[C:22](B(O)O)=[CH:21][CH:20]=[N:19]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]([NH:8][C:9]([C:11]1[S:15][C:14]([C:22]2[NH:18][N:19]=[CH:20][CH:21]=2)=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 112519791H-Pyrazole-5-boronic acidHCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

Product 1

HCID 24955764HCID 24955764, compoundYield 66%

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 benzyl amide (2.0 g, 6.43 mmol) in toluene (30 mL), water (10 mL) and ethanol (10 mL) was added 1H-pyrazole-5-boronic acid (1.44 g, 12.9 mmol), Pd(PPh3)4 (0.74 g, 0.643 mmol), and potassium carbonate (2.67 g, 19.3 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 (100 mL), and washed with brine (2×100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by preparative thin layer chromatography over silica gel (ethyl acetate:hexane, 1:1) to provide 4-methyl-2-(2H-Pyrazol-3-yl)-thiazole-5-carboxylic acid benzylamide (1.25 g, 66% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.76 (t, J=4.0 Hz, 1H), 7.89 (d, J=4.0 Hz, 1H), 7.31-7.36 (m, 4H), 7.24-7.27 (m, 1H), 6.78 (d, J=4.0 Hz, 1H), 4.44 (d, J=4.0 Hz, 2H), 2.60 (s, 3H); MS (M+H)+=299.1; Rt=1.06 min; HRMS (M+H)+=299.10.

Workup

  1. customThe resulting mixture was degassed three times
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additiondiluted with ethyl acetate (100 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 preparative thin layer chromatography over silica gel (ethyl acetate:hexane, 1:1)

Sources & evidence

ORD record
ord-512f7c82819d4adca470c0adc7d3616f
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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