Potassium Fluoride → 3-(4-tert-Butyl-phenyl)-4-cyano-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester

HRID 1990081Notes

Reaction equation

HRID 1990081 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([C:14]([F:17])([F:16])[F:15])=[C:9]([C:12]#[N:13])[C:10]=1I)=[O:5])[CH3:2].[C:18]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].[F-].[K+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)C)[C-]1C=CC=C1)(C)C.[C-]1(P(C(C)C)C(C)C)C=CC=C1.[Fe+2]>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([C:14]([F:17])([F:16])[F:15])=[C:9]([C:12]#[N:13])[C:10]=1[C:25]1[CH:26]=[CH:27][C:22]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:23][CH:24]=1)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 522689Potassium FluorideHCID 27343204-tert-Butylphenylboronic acidHCID 685208084-Cyano-3-iodo-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester

Product 1

HCID 685254973-(4-tert-Butyl-phenyl)-4-cyano-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 15420033Bis(cyclopenta-2,4-dien-1-yl-di(propan-2-yl)phosphane);iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Combine 4-cyano-3-iodo-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester (0.136 mmol) with 4-t-butyl-phenyl boronic acid (0.163 mmol), palladium acetate (0.027 mmol), 1,1′-Bis(di-i-propylphosphino)ferrocene (0.027 mmol), and potassium fluoride in DME at room temperature. Stirred at room temperature for 17 hours. Concentrated reaction in vacuo and purified by radial chromatography eluting with hexanes/methylene chloride to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 7.41 (q, 4H, J=21.7 Hz), 4.26 (q, 2H, J=7.0 Hz), 1.37 (s, 9H) and 1.21 (t, 3H, J=7.3 Hz), 19F NMR (CDCl3) δ—57.2 ppm (s).

Workup

  1. customat room temperature
  2. concentrationConcentrated
  3. customreaction in vacuo
  4. custompurified by radial chromatography
  5. washeluting with hexanes/methylene chloride

Sources & evidence

ORD record
ord-f086890992e049a08f58009a853840a8
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

Loading…