Potassium Carbonate → HCID 59320975, compound

HRID 341159Notes

Reaction equation

HRID 341159 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH3:23][N:24]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[N:25]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.C1(C)C=CC=CC=1.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>[CH2:21]([NH:20][C:18]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:8]2[N:5]3[CH:6]=[CH:7][C:2]([C:27]4[CH:26]=[N:25][N:24]([CH3:23])[CH:28]=4)=[CH:3][C:4]3=[N:10][CH:9]=2)[CH:12]=1)=[O:19])[CH3:22]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 59320890HCID 59320890, compound

Product 1

HCID 59320975HCID 59320975, compound

Reagents, catalysts & solvents 4

HCID 178418851HCID 178418851, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 1-[3-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-phenyl]-3-ethyl urea (200 mg, 0.636 mmol, 1 equivalent, made using procedure F1a), 1-methylpyrazole-4-boronic acid pinacol ester (commercially available, 265 mg, 1.272 mmol, 2 equivalents), potassium carbonate (527 mg, 3.816 mmol, 6 equivalents), and bis(tri-t-butylphosphine)palladium(0) (16 mg, 0.032 mmol, 0.05 equivalents) in ethanol (10 ml), toluene (10 ml) and water (10 ml) was heated at 70° C. for 24 h. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with a saturated brine solution, dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was purified by column chromatography (Biotage SP4, 25S, flow rate 25 ml/min, gradient 0% to 20% methanol in ethyl acetate) to give 1-ethyl-3-{3-[7-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-a]pyridin-3-yl]-phenyl}-urea as a white solid (35 mg). MS: [M+H]+ 361.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with a saturated brine solution
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customThe residue was purified by column chromatography (Biotage SP4, 25S, flow rate 25 ml/min, gradient 0% to 20% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-f608dc540ae440c9a127d5b7c97d2694
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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