Potassium Carbonate → 3-(2-{4-[4-Isopropyl-2-(2-trifluoromethyl-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-vinyl)-benzoic acid methyl ester

HRID 2261851Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=2[CH3:19])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]1[N:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:40]([F:43])([F:42])[F:41])[N:32]=[CH:31][C:30]=1[CH:44]([CH3:46])[CH3:45]>CC#N>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:28][C:29]3[N:33]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[C:40]([F:42])([F:41])[F:43])[N:32]=[CH:31][C:30]=3[CH:44]([CH3:46])[CH3:45])=[CH:14][C:13]=2[CH3:19])[CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 3-[2-(4-hydroxy-2-methyl-phenyl)-vinyl]-benzoic acid methyl ester (107 mg, 0.4 mmol) and potassium carbonate (138 mg, 1 mmol) in CH3CN (4 mL) is added 5-bromomethyl-4-isopropyl-1-(2-trifluoromethyl-phenyl)-1H-pyrazole in CH3CN (4 mL, approximately 0.1 mmol/mL). The reaction mixture is stirred at 80° C. for 5 hours and filtered through a Celite® pad eluting with EtOAc. The combined filtrate is concentrated and purified by column chromatography (0 to 20% EtOAc in hexanes) to give the desired product, 136 mg (64%).

Workup

filtrationfiltered through a Celite® pad
washeluting with EtOAc
concentrationThe combined filtrate is concentrated
custompurified by column chromatography (0 to 20% EtOAc in hexanes)

Sources & evidence

ORD record: ord-5d3c6571eb0b48179410cb94c7449350
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846960B2

Reaction notes

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