Sodium Bicarbonate → 5-Bromo-2'-chloro-3,4'-bipyridine

HRID 84175Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](I)[CH:7]=1.[Cl:9][C:10]1[CH:15]=[C:14](B(O)O)[CH:13]=[CH:12][N:11]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Br:1][C:2]1[CH:7]=[C:6]([C:14]2[CH:13]=[CH:12][N:11]=[C:10]([Cl:9])[CH:15]=2)[CH:5]=[N:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 9.63 g (33.9 mmol) 3-bromo-5-iodopyridine, 4.85 g (30.8 mmol) 2-chloro-pyridine-4-boronic acid and 3.11 g (37.0 mmol) sodium bicarbonate in 120 ml DMF and 30 ml water is heated to 80° C. under nitrogen. 433 mg (0.616 mmol) bis-(triphenylphosphine)-palladium(II)-chloride are added and the mixture is stirred for 4 hrs at 80° C. Water is added to the reaction mixture and the resulting precipitate is filtered off and washed well with water. The residue is dried under vacuum and recrystallized from 2-propanol yielding 5-bromo-2′-chloro-[3,4′]bipyridinyl as brown crystals; HPLC-MS: 2.16 min, [M+H] 271.

Workup

filtrationthe resulting precipitate is filtered off
washwashed well with water
customThe residue is dried under vacuum
customrecrystallized from 2-propanol

Sources & evidence

ORD record: ord-6390756003754857b74fc97401b37f56
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846931B2

Reaction notes

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