Реакция #53449

Уравнение реакции

1-[3-Cyano-4-fluorophenyl)-3-methyl-6-[4-bromophenyl]-1,4,5,6-tetrahydro-7H-pyrazolo-[3,4-c]-pyridin-7-one

N2

EtOAc

→

1,4,5,6-tetrahydro-7H-pyrazolo-[3,4-c]-pyridin-7-one

Растворители

C6H6

Na2CO3

brine

Условия реакции

Обработка

1. 1
   Температураthe mixture heated
2. 2
   Температураat reflux for 18 h
3. 3
   workup.ADDITIONwas added
4. 4
   Другоеthe layers separated
5. 5
   СушкаThe organic layer was dried (MgSO4)
6. 6
   Другоеevaporated
7. 7
   Другоеthe residue was purified by silica gel chromatography (100 g of SiO2, eluted with 1:1 hexane:EtOAc)

Методика

1-[3-Cyano-4-fluorophenyl)-3-methyl-6-[4-bromophenyl]-1,4,5,6-tetrahydro-7H-pyrazolo-[3,4-c]-pyridin-7-one (Example 47, Part B; 0.23 g, 0.54 mmol), 2-thiomethylphenylboronic acid (0.13 g, 0.76 mmol) and Bu4NBr (0.011 g) in C6H6 (20 mL) and 2N Na2CO3 (4 mL) was purged with a stream of N2 gas. Palladium tetrakis(triphenyl) phosphine (0.032 g, 0.028 mmol) was added and the mixture heated at reflux for 18 h. To the cooled reaction mixture, brine and EtOAc was added and the layers separated. The organic layer was dried (MgSO4) and evaporated then the residue was purified by silica gel chromatography (100 g of SiO2, eluted with 1:1 hexane:EtOAc) to give 0.17 g (3.2 mmol) of 1-[3-cyano-4-fluorophenyl]-3-methyl-6-[2′-thiomethyl)-[1,1′]-biphen-4-yl]-1,4,5,6-tetrahydro-7H-pyrazolo-[3,4-c]-pyridin-7-one; LRMS (M+H)+: 469.0 m/z.

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