Water → HCID 67500172, compound

HRID 921553Notes

Reaction equation

HRID 921553 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].[F:17][C:18]([F:39])([F:38])[C:19]1[C:27]2[C:22](=[N:23][CH:24]=[CH:25][C:26]=2[C:28]2[CH:29]=[N:30][C:31]3[C:36]([CH:37]=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)[NH:21][N:20]=1.O>CN1CCCC1=O>[CH3:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[N:21]1[C:22]2=[N:23][CH:24]=[CH:25][C:26]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:27]2[C:19]([C:18]([F:17])([F:39])[F:38])=[N:20]1)[C:6]#[N:7]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27791804-Fluoro-3-methylbenzonitrileHCID 178506293HCID 178506293, compound

Product 1

HCID 67500172HCID 67500172, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
120 °C

Procedure

4-Fluoro-3-methylbenzonitrile (0.052 g) and cesium carbonate (0.150 g) were added to a solution of compound (1d) (0.092 g) in 1-methyl-2-pyrrolidone (hereinafter referred to as NMP) (1.0 mL), followed by stirring at 120° C. for 60 hr. Water was added to the reaction solution, and the precipitate was collected by filtration and was washed by sprinkling water to obtain 3-methyl-4-{4-(quinolin-3-yl)-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile (11%). According to Example 1(7), compound (82) (64%) was prepared as a white solid using 3-methyl-4-{4-(quinolin-3-yl)-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile instead of compound (1f).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwas washed

Sources & evidence

ORD record
ord-f3cee51dfbe8474b8a9702ea35a0035b
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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