Triethylamine → 3-Chloro-5-(4-fluorophenylethynyl)-pyridine

HRID 606892Notes

Reaction equation

HRID 606892 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:17][C:18]1[CH:19]=[C:20](OS(C(F)(F)F)(=O)=O)[CH:21]=[N:22][CH:23]=1.C(OCC)(=O)C>[Cu]I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:17][C:18]1[CH:23]=[N:22][CH:21]=[C:20]([C:9]#[C:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:19]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 5226271-Ethynyl-4-fluorobenzeneHCID 151858705-Chloropyridin-3-yl trifluoromethanesulfonate

Product 1

HCID 670477483-Chloro-5-(4-fluorophenylethynyl)-pyridineYield 65%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

Add 4-fluorophenylacetylene (1.0 g, 8.35 mmol), triethylamine (4 mL, 30 mmol), copper (I) iodide (76 mg, 0.40 mmol), and bis(triphenylphosphine)palladium (II) dichloride (140 mg, 0.20 mmol) to a solution of trifluoromethanesulfonic acid 5-chloropyridin-3-yl ester, (prepared as described in PREPARATION 25) in ethyl acetate (1.95 g, 7.5 mmol), (7 mL) under nitrogen and heat at 60° C. for 12 h. Concentrate and purify the residue by silica gel chromatography, eluting with dichloromethane to give the title compound as a white solid (1.12 g, 65%).

Workup

  1. concentrationConcentrate
  2. custompurify the residue by silica gel chromatography
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-c41f0e2fa3544935a1e62064869a8e4b
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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