Sodium hydride → HCID 67500287, compound

HRID 921557Notes

Reaction equation

HRID 921557 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[N:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]=[CH:12]2)[NH:4][CH:3]=1.[H-].[Na+].[Br:24][C:25]1[CH:32]=[C:31](F)[CH:30]=[CH:29][C:26]=1[C:27]#[N:28]>CN(C=O)C>[Br:24][C:25]1[CH:32]=[C:31]([N:4]2[C:5]3=[N:6][CH:7]=[CH:8][C:9]([N:11]4[CH:15]=[C:14]([C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=5)[N:13]=[CH:12]4)=[C:10]3[C:2]([CH3:1])=[CH:3]2)[CH:30]=[CH:29][C:26]=1[C:27]#[N:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1189392-Bromo-4-fluorobenzonitrileHCID 67501397HCID 67501397, compound

Product 1

HCID 67500287HCID 67500287, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound (97c) (0.140 g) was dissolved in DMF (1.7 mL), and sodium hydride (0.024 g, a 55% dispersion in paraffin liquid) was added to the resulting solution at 0° C., followed by stirring for 10 min. Then, 2-bromo-4-fluorobenzonitrile (0.112 g) was added to the reaction solution, followed by stirring at 50° C. for 30 min. Ice water was added to the reaction solution, and the precipitate was collected by filtration and was dried under reduced pressure to obtain compound (97d) (0.160 g, 69%) as a white solid.

Workup

  1. stirringby stirring at 50° C. for 30 min
  2. filtrationthe precipitate was collected by filtration
  3. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-34736508233c4569948daef344d5716e
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

Loading…