2-Bromo-3-methylpyridine → HCID 11580951, compound
Reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.B(OBO)O.[CH3:14][C:15]([O-])=O.[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C(O)C>[CH3:8][C:7]1[C:2]([C:4]2[C:15]([CH3:14])=[CH:6][CH:7]=[CH:2][N:3]=2)=[N:3][CH:4]=[CH:5][CH:6]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
Placed 172 mg(1.0 mmol) of 2-bromo-3-methylpyridine in a reaction tube together with 281 mg (1.11 mmol) of the pinacol ester of diboronic acid, 22.5 mg Pd(OAc)2 and 300 mg (3.06 mmol) of KOAc After addition of 5 ml ethanol the mixture was warmed to 80° C. After 6 h the gc of an aliquot of the reaction mixture (extracted with ether/water) indicated the formation of the 3,3′-dimethyl-2,2′-bipyridine. The reaction was left for 65 h at 80° C. after which the only peaks detected in the gc, of the ether solution of an ether/water extracted sample of the reaction solution, were 3,3′-dimethyl-2,2′-bipyridine (gc/ms, m/z 185, M+1) and the pinacol ester of diboronic acid.
Workup
- extractionAfter 6 h the gc of an aliquot of the reaction mixture (extracted with ether/water)
Sources & evidence
- ORD record
- ord-a438186277e0436bb5a155317978c014
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06559310B2
Reaction notes
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