Potassium Carbonate → Methyl 4-[(4E)-5-(5-fluoro-2-{[4-(trifluoromethyl)benzyl]oxy}phenyl)-3-{2-[4-(methoxycarbon-yl)phenyl]ethyl}pent-4-en-1-yl]benzoate

HRID 1015934Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:21]=[CH:22][C:23]([OH:53])=[C:24](/[CH:26]=[CH:27]/[CH:28]([CH2:41][CH2:42][C:43]2[CH:48]=[CH:47][C:46]([C:49]([O:51][CH3:52])=[O:50])=[CH:45][CH:44]=2)[CH2:29][CH2:30][C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)[CH:25]=1>C(#N)C>[F:19][C:20]1[CH:21]=[CH:22][C:23]([O:53][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=2)=[C:24](/[CH:26]=[CH:27]/[CH:28]([CH2:41][CH2:42][C:43]2[CH:48]=[CH:47][C:46]([C:49]([O:51][CH3:52])=[O:50])=[CH:45][CH:44]=2)[CH2:29][CH2:30][C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)[CH:25]=1

Participants

Conditions

Temperature: 60 °C

Procedure

280 mg (1.2 mmol) of 1-(bromomethyl)-4-(trifluoromethyl)benzene and 162 mg (1.2 mmol) of anhydrous potassium carbonate are added to a solution of 279 mg (0.59 mmol) of methyl 4-[(4E)-5-(5-fluoro-2-hydroxyphenyl)-3-{2-[4-(methoxycarbonyl)phenyl]ethyl} pent-4-en-1-yl]benzoate in 6.5 ml of dry acetonitrile, and the mixture is then heated at 60° C. for 12 hours. The mixture is then filtered, and the filtrate is evaporated to dryness. The residue is purified by preparative HPLC. This gives 274 mg (0.43 mmol, 74% of theory) of a colorless oil.

Workup

filtrationThe mixture is then filtered
customthe filtrate is evaporated to dryness
customThe residue is purified by preparative HPLC

Sources & evidence

ORD record: ord-1119bf46909c46fcb28a6e815541bf01
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985876B2

Reaction notes

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