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

HRID 606848Notes

Reaction equation

HRID 606848 reaction equation
C(N(CC)CC)C.Br[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[CH:24])[CH:18]=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:15][C:13]1[CH:12]=[N:11][CH:10]=[C:9]([C:24]#[C:23][C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([Cl:16])[CH:18]=2)[CH:14]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 693693,5-DibromopyridineHCID 1230861-Chloro-3-ethynylbenzene

Product 1

HCID 670475933-Bromo-5-(3-chlorophenylethynyl)-pyridineYield 46.2%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
50 °C

Procedure

Add triethylamine (2.38 mL, 16.88 mmol), copper (I) iodide (80.4 mg, 0.422 mmol) and bis(triphenylphosphine)palladium (II) dichloride (148 mg, 0.211 mmol) to a solution of 3,5-dibromopyridine (1 g, 4.22 mmol) and 1-chloro-3-ethynylbenzene, (prepared as described in PREPARATION 12), (574 mg, 4.22 mmol) in ethyl acetate (4.22 mL). Stir under nitrogen at 50° C. for 18 h. Concentrate and purify the residue by silica gel chromatography, eluting with 100:0 to 0:100 hexanes:ethyl acetate, to give the title compound (571 mg, 46%).

Workup

  1. concentrationConcentrate
  2. custompurify the residue by silica gel chromatography
  3. washeluting with 100:0 to 0:100 hexanes

Sources & evidence

ORD record
ord-a5ea1f42ceb44f978be9fd8bb0227719
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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