[CH3:1][O-:2].[Na+].Br[N:5]1[C:9](=[O:10])CCC1=O.[N:12]1([C:18]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH3:33])[C:21](C(N)=O)=[CH:20][N:19]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.Cl>ClCCl>[CH3:1][O:2][C:9](=[O:10])[NH:5][C:21]1[CH:20]=[N:19][C:18]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[CH:26][C:25]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33]9.9 ml (53.7 mMol) Sodium methoxide solution (5.4 M in MeOH) were added over 15 minutes to a solution of 3.9 g (21.5 mMol) N-bromosuccinimide in 22.5 ml dichloromethane cooled to −5° C. The milky suspension was stirred at −5° C. for 18 hours, then, at the same temperature, a solution of 4.5 g (14 mMol) 6-morpholin-4-yl-4-o-tolyl-nicotinamide in 22.5 ml dichloromethane was added over 15 minutes. After 5 hours at 5° C., 33 ml (33 mMol) aqueous HCl 1N were added, the phases were separated, the organic phase washed with water and the aqueous phases extracted with dichloromethane. The combined organic phases were dried (Na2SO4) and evaporated. The residue was treated with basic Alox (1:1 weight) in ethyl acetate/heptane 1:1 for 30 minutes at room temperature. After filtration and removal of the solvents, the residue was crystallized from di-iso-propylether/n-heptane 1:2 at OOC to yield 3.4 g (72.5%) (6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-carbamic acid methyl ester as a yellow powder.
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