2,5-Dibromopyridine → {4-[4-(5-Bromo-pyridin-2-yl)-but-3-ynyl]-phenyl}-methanol

HRID 1916537Notes

Reaction equation

HRID 1916537 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][CH:6]=1)[CH2:2][C:3]#[CH:4].Br[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1>C(N(CC)CC)C.C(Cl)Cl.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([C:4]#[C:3][CH2:2][CH2:1][C:5]2[CH:6]=[CH:7][C:8]([CH2:11][OH:12])=[CH:9][CH:10]=2)=[N:15][CH:16]=1

Participants

7

Reactant 2

HCID 693532,5-DibromopyridineHCID 235966094-(3-Butyn-1-yl)benzenemethanol

Product 1

HCID 69070552{4-[4-(5-Bromo-pyridin-2-yl)-but-3-ynyl]-phenyl}-methanol

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

Under an N2 atmosphere 130 mg (0.67 mmol) CuI and 300 mg (0.42 mmol) Pd(PPh3)2Cl2 are added to a solution of 2.0 g (12.48 mmol) (4-but-3-ynyl-phenyl)-methanol and 3.2 g (13.1 mmol) 2,5-dibromopyridine in 80 mL triethylamine and the reaction mixture is stirred for 1.5 h at 50° C. The solvent is eliminated in vacuo, the residue dissolved in a little DCM and purified by chromatography on silica gel (gradient: cyc/EtOAc 4:1 to cyc/EtOAc 3:1).

Workup

  1. custompurified by chromatography on silica gel (gradient: cyc/EtOAc 4:1 to cyc/EtOAc 3:1)

Sources & evidence

ORD record
ord-6b15665bd4dd4132a87207ea712638f1
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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