Hydrochloric Acid → 2-[2-(4-Pyridin-2-ylphenyl)-2H-tetrazol-5-yl]pyridine

HRID 734253Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[N:12]=[N:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:9]2)=[CH:4][CH:3]=1.[Br-].[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Zn+].Cl.CCOCC>C1COCC1>[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[N:12]=[N:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-[2-(4-bromophenyl)-2H-tetrazol-5-yl]pyridine (300 mg, 1 mmol), 2-pyridylzinc bromide (0.5M in THF, 2 mL) and tetrakis-(triphenylphosphine)palladium(0) (100 mg, 0.085 mmol) in anhydrous THF (10 mL) was degassed for 15 min and heated to 60° C. After 4 hours, a further equivalent of 2- pyridylzinc bromide (0.5M in THF, 2 mL) was added and the reaction mixture was heated at reflux overnight. The reaction mixture was then quenched with brine (25 mL), extracted with EtOAc (3×25 mL), dried over Na2SO4 and concentrated in vacuo. The crude residue was chromotographed on silica gel, eluting with EtOAc to afford a yellow solid. This was dissolved in anhydrous THF (10 mL) and HCl in ether (1.5 equiv) was added and the resulting precipitate was filtered to afford a yellow solid.

Workup

temperaturethe reaction mixture was heated
temperatureat reflux overnight
customThe reaction mixture was then quenched with brine (25 mL)
extractionextracted with EtOAc (3×25 mL)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
washeluting with EtOAc
customto afford a yellow solid
filtrationthe resulting precipitate was filtered
customto afford a yellow solid

Sources & evidence

ORD record: ord-3bac79dfd6e24a74b03eca08c1bba1d2
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592337B2

Reaction notes

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