Tetrahydrofuran → 3-(5-Bromopyridin-3-ylethynyl)-benzonitrile

HRID 606801Notes

Reaction equation

HRID 606801 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.Br[C:25]1[CH:26]=[N:27][CH:28]=[C:29]([Br:31])[CH:30]=1.C[Si]([C:36]#[C:37][C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=1)[C:41]#[N:42])(C)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>[Br:31][C:29]1[CH:30]=[C:25]([C:36]#[C:37][C:38]2[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=2)[C:41]#[N:42])[CH:26]=[N:27][CH:28]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 693693,5-DibromopyridineHCID 2724141Tetrabutylammonium FluorideHCID 225703183-[(Trimethylsilyl)ethynyl]benzonitrile

Product 1

HCID 670476833-(5-Bromopyridin-3-ylethynyl)-benzonitrileYield 39%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalyst

Procedure

Prepare essentially as described in PREPARATION 17 using a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (4.2 mL, 4.2 mmol), 3,5-dibromopyridine (1.00 g, 4.2 mmol), 3-trimethylsilanylethynylbenzonitrile (0.84 g, 4.2 mmol), (prepared as described in PREPARATION 5), bis(triphenylphosphine)palladium (II) dichloride (0.06 g, 0.08 mmol) and copper (I) iodide (0.03 g, 0.17 mmol) to give the title compound (0.45 g, 39%).

Workup

  1. customPrepare essentially

Sources & evidence

ORD record
ord-be713fc415824b8fb317b84e44f112d7
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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