Potassium Carbonate → 1-(2'-t-Butoxycarbonyl-3-fluorobiphenyl-4-ylmethyl)-5-propyl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1803786Notes

Reaction equation

[CH2:1]([C:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:6][N:5]=1)[CH2:2][CH3:3].[C:14]([O:18][C:19]([C:21]1[C:22]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33]Br)=[C:29]([F:35])[CH:28]=2)=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:12]([O:11][C:9]([C:7]1[CH:8]=[C:4]([CH2:1][CH2:2][CH3:3])[N:5]([CH2:33][C:30]2[CH:31]=[CH:32][C:27]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[C:19]([O:18][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:20])=[CH:28][C:29]=2[F:35])[N:6]=1)=[O:10])[CH3:13]

Participants

Conditions

Temperature: 65 °C

Procedure

Ethyl 3-n-propylpyrazole-5-carboxylate (1.05 g, 5.8 mmol), 4′-bromomethyl-3′-fluorobiphenyl-2-carboxylic acid t-butyl ester (2.0 g, 5.8 mmol), and potassium carbonate (1.6 g, 11.5 mmol) were dissolved in DMF (10 mL). The mixture was stirred at 65° C. for 16 hours, then diluted with EtOAc. The organic layer was washed with saturated NaHCO3 and saturated aqueous NaCl, and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash chromatography (EtOAc in hexanes) to yield 1-(2′-t-butoxycarbonyl-3-fluorobiphenyl-4-ylmethyl)-5-propyl-1H-pyrazole-3-carboxylic acid ethyl ester (2.7 g).

Workup

washThe organic layer was washed with saturated NaHCO3 and saturated aqueous NaCl
dry with materialdried over Na2SO4
customThe solvent was removed in vacuo
customthe residue was purified by flash chromatography (EtOAc in hexanes)

Sources & evidence

ORD record: ord-54b51baa933143a9bb4c2787a2a84762
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08350027B2

Reaction notes

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