Sodium Cyanide → HCID 87538453, compound

HRID 1444543Notes

Reaction equation

HRID 1444543 reaction equation
Cl[C:2]1[C:3]([OH:31])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([NH:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]=1[CH:15]=[CH:16][NH:17][C:18]3=[O:23])[C:7]([OH:28])([C:24]([F:27])([F:26])[F:25])[CH2:6][C:5]2([CH3:30])[CH3:29].[C-:32]#[N:33].[Na+]>CN1CCCC1=O.[Ni](Br)Br>[OH:31][C:3]1[C:4]2[C:5]([CH3:30])([CH3:29])[CH2:6][C:7]([OH:28])([C:24]([F:25])([F:27])[F:26])[CH:8]([NH:12][C:13]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:14]=3[CH:15]=[CH:16][NH:17][C:18]4=[O:23])[C:9]=2[CH:10]=[CH:11][C:2]=1[C:32]#[N:33]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 87539079HCID 87539079, compound

Product 1

HCID 87538453HCID 87538453, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 278492Nickel(II) bromideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

75 mg (0.166 mmol) of 5-(6-chloro-2,5-dihydroxy-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalin-1-ylamino)-2H-isoquinolin-1-one is dissolved in 1.3 ml of 1-methyl-2-pyrrolidinone and reacted in the microwave with 16.27 mg (0.332 mmol) of sodium cyanide and 36.27 mg (0.166 mmol) of nickel(II) bromide as described in Example 160. The black reaction mixture is added through a glass-fiber filter. After washing with ethyl acetate, the filtrate is mixed with an additional 60 ml of ethyl acetate. It is shaken with water and with brine. After drying, the solvent is spun off, and the residue is chromatographed on silica gel (amine plate: mobile solvent methanol/dichloromethane). 16.2 mg (22.1%) of the desired nitrile is isolated.

Workup

  1. customThe black reaction mixture
  2. additionis added through a glass-fiber
  3. filtrationfilter
  4. washAfter washing with ethyl acetate
  5. additionthe filtrate is mixed with an additional 60 ml of ethyl acetate
  6. customAfter drying
  7. customthe residue is chromatographed on silica gel (amine plate: mobile solvent methanol/dichloromethane)

Sources & evidence

ORD record
ord-d8639b7512024ac6a2309a6861cca089
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

Loading…