Triethylamine → 3-Bromo-5-(3-trifluoromethylphenylethynyl)-pyridine

HRID 606852Notes

Reaction equation

HRID 606852 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]#[CH:16])[CH:14]=1.I[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=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>[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]#[C:16][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[CH:14]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 67868Benzene, 1-iodo-3-(trifluoromethyl)-HCID 154238793-Bromo-5-ethynylpyridine

Product 1

HCID 665244133-Bromo-5-(3-trifluoromethylphenylethynyl)-pyridineYield 61%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Add triethylamine (6.2 mL, 44 mmol), copper (I) iodide (120.3 mg, 1.10 mmol) and bis(triphenylphosphine)palladium (II) dichloride (386 mg, 0.55 mmol) to a solution of 3-bromo-5-ethynylpyridine, (prepared essentially as described in PREPARATION 23), (2.0 g, 11 mmol) and 1-iodo-3-trifluoromethylbenzene (1.53 mL, 11 mmol) in ethyl acetate (12 mL). Stir at room temperature for 18 h. Concentrate and purify the residue by silica gel chromatography, eluting with 100:0 to 100:50 hexanes:ethyl acetate to give the title compound (2.1 g, 61%).

Workup

  1. custom(prepared essentially
  2. concentrationConcentrate
  3. custompurify the residue by silica gel chromatography
  4. washeluting with 100:0 to 100:50 hexanes

Sources & evidence

ORD record
ord-243dec94bdc749e88c1b3ce94ce258d8
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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