Potassium Carbonate → HCID 117729570, compound

HRID 711151Notes

Reaction equation

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

Participants

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-fluorophenol (1.00 g, 5.23 mmol), 3-tert-butyl-1H-pyrazole-5-amine (728 mg, 5.23 mmol), copper (I) iodide (50.0 mg, 0.26 mmol) and potassium carbonate (1.52 g, 11.0 mmol). Trans-N,N′-dimethylcyclohexanediamine (165 μL, 1.05 mmol) was added and the reaction heated to 150° C. for 3.5 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 0-75% EtOAc in cyclohexane, to give the title compound (488 mg, 37%). LCMS (Method 4): Rt 2.49 min, m/z 250 [MH+].

Workup

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

Sources & evidence

ORD record: ord-1c817c8f7ad7433fbb7e23e9fee1ffe9
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181242B2

Reaction notes

Loading…