5-Bromo-2-methoxypyridine → (R)-3-(4-Bromophenyl)-1-(6-methoxypyridin-3-yl)-3-o-tolylpropan-1-one

HRID 1617736Notes

Reaction equation

HRID 1617736 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]([C@H:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[CH2:23][C:24](N(OC)C)=[O:25])=[CH:18][CH:17]=1>>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([C@H:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[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:20][CH:21]=1

Participants

4

Reactant 3

HCID 27348955-Bromo-2-methoxypyridineHCID 71813344(R)-3-(4-Bromophenyl)-N-methoxy-N-methyl-3-o-tolylpropanamideHCID 178418339Butyllithium

Product 1

HCID 67015570(R)-3-(4-Bromophenyl)-1-(6-methoxypyridin-3-yl)-3-o-tolylpropan-1-one

Procedure

In analogy to example 151, step 1, 5-bromo-2-methoxypyridine was reacted first with n-butyllithium and later with (R)-3-(4-bromo-phenyl)-N-methoxy-N-methyl-3-o-tolyl-propionamide (example 142, step 1) to give the title compound as a colorless oil, MS (ESI+): m/z=410.1 [M+H]+.

Sources & evidence

ORD record
ord-b703aa2079ed4320ac39aa6f7c8d661e
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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