3,5-Dibromopyridine → 3-(3-Bromo-phenyl)-1-(5-bromo-pyridin-3-yl)-3-o-tolyl-propan-1-one

HRID 1617568Notes

Reaction equation

HRID 1617568 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH2:9][C:10](N(OC)C)=[O:11])[CH:5]=[CH:6][CH:7]=1.Br[C:24]1[CH:25]=[N:26][CH:27]=[C:28]([Br:30])[CH:29]=1.C([Mg]Br)(C)C>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH2:9][C:10]([C:24]2[CH:25]=[N:26][CH:27]=[C:28]([Br:30])[CH:29]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 693693,5-DibromopyridineHCID 866609653-(3-Bromo-phenyl)-N-methoxy-N-methyl-3-o-tolyl-propionamideHCID 178418365HCID 178418365, compound

Product 1

HCID 670155683-(3-Bromo-phenyl)-1-(5-bromo-pyridin-3-yl)-3-o-tolyl-propan-1-one

Procedure

In analogy to example 74, step 5, from 3-(3-bromo-phenyl)-N-methoxy-N-methyl-3-o-tolyl-propionamide (example 98, step 4) and 3,5-dibromopyridine (CAS RN: [625-92-3]) using i-propylmagnesium bromide instead of n-butyllithium was prepared the title compound as a white solid, MS (ESI+): m/z=457.9738 ([M+H]+, 1Br).

Sources & evidence

ORD record
ord-356d100575674de3aac029f37180b4ad
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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