2-(Dimethylamino)ethanol → 2-Bromo-6-chloro-4-methylpyridine

HRID 2427864Notes

Reaction equation

HRID 2427864 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.C([Li])CCC.CN(CCO)C.C(Br)(Br)(Br)[Br:21]>CCCCCC.C1COCC1>[Br:21][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([Cl:1])[N:3]=1

Participants

7

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11205Carbon tetrabromideHCID 772482-Chloro-4-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 111172342-Bromo-6-chloro-4-methylpyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Starting with 2-chloro-4-methylpyridine II, treatment with n-butyllithium in the presence of N,N-dimethylaminoethanol in hexane, followed by addition of carbon tetrabromide in THF affords 2-bromo-6-chloro-4-methylpyridine III. Compound III undergoes a palladium coupling with boronic acid IV in the presence of a base, such as Na2CO3, in a suitable solvent, such as DME, to give chloropyridine V.

Sources & evidence

ORD record
ord-e75ca494381245ac8e0a1cb0c2f4ee1c
Source dataset
uspto-grants-2011_06
Patent number
US07968725B2

Reaction notes

Loading…