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

HRID 734254Notes

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.C(=O)([O-])[O-].[K+].[K+].[N:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.Cl>COCCOC.O.C1COCC1.CCOCC>[N:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[N:12]=[N:11][C:10]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=4)=[N:9]3)=[CH:4][CH:3]=2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 2-[2-(4-bromophenyl)-2H-tetrazol-5-yl]pyridine (300 mg, 1 mmol), potassium carbonate (0.276 g, 2.0 mmol), and pyridin-4-ylboronic acid (123 mg, 1 mmol) in ethylene glycol dimethyl ether (20 mL) and water (4 mL) was degassed with argon for 15 min. Then tetrakis (triphenylphosphine)palladium(0) (80 mg, 0.068 mmol) was added, the mixture degassed for another 15 min, and the solution was stirred at 65° C. for 12 h. The reaction mixture was then quenched with water (30 mL), extracted with EtOAc (3×30 mL) and washed with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude residue was chromatographed on silica gel, eluting with EtOAc to afford a yellow solid. This was dissolved in anhydrous THF (10 mL) and HCl (1.5equiv) in ether was added. The

Workup

customthe mixture degassed for another 15 min
customThe reaction mixture was then quenched with water (30 mL)
extractionextracted with EtOAc (3×30 mL)
washwashed with brine
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated in vacuo
customThe crude residue was chromatographed on silica gel
washeluting with EtOAc
customto afford a yellow solid

Sources & evidence

ORD record: ord-069ff4c8ae8544c4b0f094dcfbe591ad
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592337B2

Reaction notes

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