Ethyl Acetate → 3-Fluoro-4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoic acid methyl ester

HRID 1669323Notes

Reaction equation

HRID 1669323 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([CH:15]([OH:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:25][O:26][C:27](=[O:36])[C:28]1[CH:33]=[CH:32][C:31](O)=[C:30]([F:35])[CH:29]=1.C(P(CCCC)CCCC)CCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:25][O:26][C:27](=[O:36])[C:28]1[CH:33]=[CH:32][C:31]([O:22][CH:15]([C:12]2[CH:13]=[N:14][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:23])([F:1])[F:24])=[CH:8][CH:7]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[C:30]([F:35])[CH:29]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 13831TributylphosphineHCID 7019368Methyl 3-fluoro-4-hydroxybenzoateHCID 597294261-[6-(4-Trifluoromethyl-phenyl)-pyridin-3-yl]-heptan-1-ol

Product 1

HCID 673420373-Fluoro-4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoic acid methyl esterYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Combine 1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptan-1-ol (0.050 g, 0.15 mmol) and 3-fluoro-4-hydroxy-benzoic acid methyl ester (0.030 g, 0.18 mmol) in toluene (0.5 mL). Add 1,1′-(diazocarbonyl)dipiperidine (0.057 g, 0.23 mmol) followed by tributyl-phosphine (0.06 mL, 0.23 mmol) under inert atmosphere. Stir at room temperature for 16 hours. Dilute reaction with ethyl acetate filter and remove solvent under reduced pressure. Purify on silica gel chromatography (0-40% ethyl acetate/hexane gradient) to provide 0.04 g of title compound (57%).

Workup

  1. additionDilute
  2. filtrationfilter
  3. customremove solvent under reduced pressure
  4. customPurify on silica gel chromatography (0-40% ethyl acetate/hexane gradient)

Sources & evidence

ORD record
ord-2f5d59a80d184d05a9a70aca7a3be0b1
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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