Potassium Carbonate → HCID 68489655, compound

HRID 1879209Notes

Reaction equation

HRID 1879209 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]([C:10]2[S:14][C:13](Br)=[N:12][C:11]=2[CH3:16])=[O:9])=[CH:4][CH:3]=1.[NH:19]1[C:23](B(O)O)=[CH:22][CH:21]=[N:20]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>[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]([C:10]2[S:14][C:13]([C:23]3[NH:19][N:20]=[CH:21][CH:22]=3)=[N:12][C:11]=2[CH3:16])=[O:9])=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 112519791H-Pyrazole-5-boronic acidHCID 666314052-Bromo-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide

Product 1

HCID 68489655HCID 68489655, compound

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 4-fluoro-benzylamide (5.0 g, 15.0 mmol) in toluene (30 mL), water (10 mL) and ethanol (10 mL) was added 1H-pyrazole-5-boronic acid (1.70 g, 15.0 mmol), Pd(PPh3)4 (1.75 g, 1.52 mmol), and potassium carbonate (6.3 g, 45.6 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 chromatography over silica gel (ethyl acetate:hexane, 50:50) to provide 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid 4-fluoro-benzylamide as yellow solid (3.25 g 68%) MS (M+H)+=317; Rt=1.13 min; HRMS (M+H)+=317.

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 chromatography over silica gel (ethyl acetate:hexane, 50:50)

Sources & evidence

ORD record
ord-59e517169dc54220a0e4445a17befec4
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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