1-Fluoro-4-iodo-2-(trifluoromethyl)benzene → 3-Chloro-5-(4-fluoro-3-trifluoromethylphenylethynyl)-pyridine

HRID 606891Notes

Reaction equation

HRID 606891 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]#[CH:9])[CH:7]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][C:12]=1[C:18]([F:21])([F:20])[F:19]>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>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]#[C:9][C:14]2[CH:15]=[CH:16][C:11]([F:10])=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[CH:7]=1

Participants

6

Reactant 2

HCID 27373441-Fluoro-4-iodo-2-(trifluoromethyl)benzeneHCID 235008873-Chloro-5-ethynylpyridine

Product 1

HCID 670483593-Chloro-5-(4-fluoro-3-trifluoromethylphenylethynyl)-pyridineYield 88%

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

Sequentially add 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (300 mg, 2.2 mmol), (bis(triphenylphosphine)palladium (II) dichloride (69 mg, 0.10 mmol), and copper (I) iodide (38 mg, 0.198 mmol) to a solution of 1-fluoro-4-iodo-2-trifluoromethylbenzene (575 mg, 1.98 mmol) in triethylamine (4 mL) under nitrogen. Heat at 70° C. for 2.5 h and concentrate. Purify the residue by silica gel chromatography, eluting from 0:100 to 20:80 using ethyl acetate:hexanes, to give the title compound as a white solid (520 mg, 88%).

Workup

  1. concentrationconcentrate
  2. customPurify the residue by silica gel chromatography
  3. washeluting from 0:100 to 20:80 using ethyl acetate

Sources & evidence

ORD record
ord-2a8e1e6ecb284ae19d0f644b99323eaa
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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