Sodium Carbonate → HCID 61025921, compound

HRID 1480837Notes

Reaction equation

HRID 1480837 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.[CH3:10][N:11]1[CH:15]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH:13]=[N:12]1.C(=O)([O-])[O-].[Na+].[Na+]>CCO.C1(C)C=CC=CC=1.O.CCOC(C)=O.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>[CH3:9][C:4]1[CH:3]=[C:2]([C:14]2[CH:13]=[N:12][N:11]([CH3:10])[CH:15]=2)[CH:8]=[CH:7][C:5]=1[NH2:6]

Participants

9

Reactant 3

HCID 10340Sodium CarbonateHCID 114234-Bromo-2-methylanilineHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 61025921HCID 61025921, compoundYield 21%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-bromo-2-methylaniline (500 mg, 2.69 mmol) in EtOH (10 mL), toluene (10 mL) and water (10 mL) was added 1-methylpyrazole-4-boronic acid pinacol ester (671 mg, 3.22 mmol), sodium carbonate (570 mg, 5.37 mmol) and Pd(PPh3)4 (373 mg, 0.322 mmol). The reaction mixture was heated to 80° C. for 2.5 hours. The reaction mixture was cooled to room temperature and diluted with EtOAc (30 mL), washed with water (30 mL) and brine (30 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by passage through a SCX-2 cartridge eluting with 100% MeOH—1M NH3 in MeOH. The residue was purified by silica gel column chromatography eluting with 0-10% MeOH in DCM to give the title compound (106 mg, 21%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water (30 mL) and brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by passage through a SCX-2 cartridge
  6. washeluting with 100% MeOH—1M NH3 in MeOH
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-7c4601b8392b4bc49023538e07b11b4b
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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