5-Bromo-2-methoxypyridine → 3-(4-Bromophenyl)-3-(4-chloro-2-methylphenyl)-1-(6-methoxypyridin-3-yl)propan-1-one

HRID 1617744Notes

Reaction equation

HRID 1617744 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C([Li])CCC.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[CH3:37])[CH2:23][C:24](N(OC)C)=[O:25])=[CH:18][CH:17]=1>>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[CH3:37])[CH2:23][C:24]([C:2]2[CH:7]=[N:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)=[O:25])=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 27348955-Bromo-2-methoxypyridineHCID 86660998HCID 86660998, compoundHCID 178418339Butyllithium

Product 1

HCID 670157173-(4-Bromophenyl)-3-(4-chloro-2-methylphenyl)-1-(6-methoxypyridin-3-yl)propan-1-one

Procedure

In analogy to example 151, step 1, 5-bromo-2-methoxypyridine was reacted first with n-butyllithium and later with 3-(4-bromophenyl)-3-(4-chloro-2-methylphenyl)-N-methoxy-N-methylpropanamide (example 138, step 3) to give the title compound as a light yellow oil, MS (ESI+): m/z=446.03 [M+H]+.

Sources & evidence

ORD record
ord-2f7e5d0dafa946e6a3417de77c1fe300
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

Loading…