Potassium Carbonate → HCID 117729787, compound

HRID 711149Notes

Reaction equation

HRID 711149 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][OH:6].[C:11]([C:15]1[CH:19]=[C:18]([NH2:20])[NH:17][N:16]=1)([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>[Cu]I>[NH2:20][C:18]1[N:17]([C:2]2[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([F:10])[CH:9]=2)[N:16]=[C:15]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2769402(3-Bromo-5-fluorophenyl)methanolHCID 178441179HCID 178441179, compound

Product 1

HCID 117729787HCID 117729787, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
150 °C

Procedure

Degassed toluene (sparged with argon for 25 mins, 10.0 mL) was added to a mixture of 3-bromo-5-fluorobenzylalcohol (1.00 g, 4.88 mmol), 3-tert-butyl-1H-pyrazole-5-amine (678 mg, 4.88 mmol), copper (I) iodide (46.0 mg, 0.24 mmol) and potassium carbonate (1.41 g, 10.2 mmol). Trans-N,N′-dimethylcyclohexanediamine (154 μL, 0.98 mmol) was added and the reaction heated to 150° C. for 18 h using microwave irradiation. The mixture was partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-100% EtOAc in cyclohexane, to give the title compound (307 mg, 24%). LCMS (Method 4): Rt 2.34 min, m/z 264 [MH+].

Workup

  1. customDegassed toluene (sparged with argon for 25 mins, 10.0 mL)
  2. custommicrowave irradiation
  3. customThe mixture was partitioned between EtOAc and water
  4. extractionThe aqueous layer was then extracted with EtOAc (3×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-18787285ef6449fd81e060df92b7040e
Source dataset
uspto-grants-2015_11
Patent number
US09181242B2

Reaction notes

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