Potassium Carbonate → Methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-{1-[2-(methyloxy)ethyl]-1H-pyrazol-4-yl}benzoate
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[N:22][NH:23][CH:24]=3)=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.[CH3:25][O:26][CH2:27][CH2:28]Br.C(=O)([O-])[O-].[K+].[K+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:17]([C:20]3[CH:24]=[N:23][N:22]([CH2:28][CH2:27][O:26][CH3:25])[CH:21]=3)=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1Participants
Procedure
To a solution of methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-(1H-pyrazol-4-yl)benzoate (may be prepared as described in Description 115; 200 mg, 0.61 mmol) was added 2-bromoethyl methyl ether (0.10 ml, 1.23 mmol), potassium carbonate (254 mg, 1.84 mmol) and the reaction mixture was stirred at room temperature. The reaction mixture was then warmed to 50° C. for 5 hours. The reaction was filtered to remove the potassium carbonate, and the organics were evaporated on a buchi under reduced pressure. The solid was taken up into ethyl acetate (50 ml) and this was washed with water (1×25 ml). The organics were dried (MgSO4) and evaporated under reduced pressure on a buchi to yield the title compound. The crude product was used directly without further purification. 240 mg.
Workup
- temperatureThe reaction mixture was then warmed to 50° C. for 5 hours
- filtrationThe reaction was filtered
- customto remove the potassium carbonate
- customthe organics were evaporated on a buchi under reduced pressure
- washthis was washed with water (1×25 ml)
- dry with materialThe organics were dried (MgSO4)
- customevaporated under reduced pressure on a buchi
Sources & evidence
- ORD record
- ord-3b795812e2224438afebcdd336239cc7
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778939B2
Reaction notes
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