Triethylamine → 3-Fluoro-5-phenylethynylpyridine

HRID 606844Notes

Reaction equation

HRID 606844 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:16][C:17]1[CH:18]=[C:19](OS(C(F)(F)F)(=O)=O)[CH:20]=[N:21][CH:22]=1>C(OCC)(=O)C.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>[F:16][C:17]1[CH:22]=[N:21][CH:20]=[C:19]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 11413882Methanesulfonic acid, trifluoro-, 5-fluoro-3-pyridinyl ester

Product 1

HCID 670474963-Fluoro-5-phenylethynylpyridineYield 65%

Reagents, catalysts & solvents 2

HCID 178419050HCID 178419050, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Add phenylacetylene (0.180 mL, 1.6 mmol), copper (I) iodide (0.015 g, 0.08 mmol) bis(triphenylphosphine)palladium (II) dichloride (0.027 g. 0.04 mmol) and triethylamine (0.85 mL, 6 mmol) to a solution of trifluoromethanesulfonic acid 5-fluoro-pyridin-3-yl ester, (prepared essentially as described in PREPARATION 6), (0.367 g, 1.5 mmol) in degassed ethyl acetate (1.5 mL) and heat at 60° C. for 16 h. Cool the reaction mixture to room temperature, filter through diatomaceous earth, wash with ethyl acetate, and concentrate. Purify the residue by silica gel chromatography, eluting with dichloromethane, to give the title compound (0.192 g, 65%).

Workup

  1. custom(prepared essentially
  2. temperatureCool the reaction mixture to room temperature
  3. filtrationfilter through diatomaceous earth
  4. washwash with ethyl acetate
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-55c22a639733475fa7dc8b4eaaabb4ef
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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