1-Fluoro-4-iodo-2-(trifluoromethyl)benzene → 3-(4-Fluoro-3-trifluoromethylphenylethynyl)-5-methoxypyridine

HRID 606885Notes

Reaction equation

HRID 606885 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[C:13]([C:15]1[CH:16]=[N:17][CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1)#[CH:14]>C(N(CC)CC)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.[Cu]I>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:14]#[C:13][C:15]2[CH:16]=[N:17][CH:18]=[C:19]([O:21][CH3:22])[CH:20]=2)=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10]

Participants

6

Reactant 2

HCID 27373441-Fluoro-4-iodo-2-(trifluoromethyl)benzeneHCID 210973493-Ethynyl-5-methoxypyridine

Product 1

HCID 670476953-(4-Fluoro-3-trifluoromethylphenylethynyl)-5-methoxypyridineYield 99.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve 1-fluoro-4-iodo-2-trifluoromethylbenzene (813 mg, 2.8 mmol) in triethylamine (6 mL). Add 3-ethynyl-5-methoxypyridine, (prepared as described in PREPARATION 10), (400 mg, 3.0 mmol) followed by bis(triphenylphosphine)palladium (II) dichloride (0.100 g, 0.14 mmol) and copper (I) iodide (53 mg, 0.28 mmol). Heat at 70° C. for 16 h, concentrate, and purify using silica gel chromatography, eluting with 100:0 to 90:10 methylene chloride:ethyl acetate, to give the title compound as a pale yellow solid (820 mg, 99%).

Workup

  1. concentrationconcentrate
  2. custompurify
  3. washeluting with 100:0 to 90:10 methylene chloride

Sources & evidence

ORD record
ord-7f8e827fe50c4c84ba3a38bd54dc5245
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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