Реакция #1509577

Уравнение реакции

1-[1-(4-Chloro-3-methyl-benzyl)-piperidin-4-yl]-5-oxo-pyrrolidine-2-carboxylic acid [3-bromo-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-amide

triethylamine

DMF

MeOH

→

title compound

3-({1-[1-(4-Chloro-3-methyl-benzyl)-piperidin-4-yl]-5-oxo-pyrrolidine-2-carbonyl}-amino)-5-(1-methyl-1H-tetrazol-5-yl)-benzoic acid methyl ester

Условия реакции

Обработка

1. 1
   ФильтрацияThe reaction mixture was filtered
2. 2
   Концентрированиеthe filtrate concentrated in vacuum
3. 3
   ДругоеThe residue was partitioned between water and EtOAc
4. 4
   Другоеthe organic layer was then separated
5. 5
   Другоеdried
6. 6
   Концентрированиеconcentrated in vacuum
7. 7
   ДругоеThe residue was purified by flash chromatography (DCM: MeOH 100:0 to 95:5 gradient)

Методика

To a solution of 1-[1-(4-Chloro-3-methyl-benzyl)-piperidin-4-yl]-5-oxo-pyrrolidine-2-carboxylic acid [3-bromo-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-amide (400 mg) in MeOH (20 ml) was added triethylamine (140 μl), DMF (5 ml), and [1,1′-bis(diphenylphosphino)-ferrocen]palladium (II) chloride (50 mg) and the reaction stirred for 2 d at 80° C. under a 3 bar CO atmosphere. The reaction mixture was filtered and the filtrate concentrated in vacuum. The residue was partitioned between water and EtOAc and the organic layer was then separated, dried and concentrated in vacuum. The residue was purified by flash chromatography (DCM: MeOH 100:0 to 95:5 gradient) to give the title compound (400 mg). Rf=0.37 (95:5 DCM:MeOH).

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