Water → HCID 87539088, compound

HRID 1869416Notes

Reaction equation

HRID 1869416 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[CH:8]([NH:12][C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[C:7]([C:20]([F:23])([F:22])[F:21])([OH:19])[CH2:6][C:5]([CH3:25])([CH3:24])[C:4]=2[C:3]=1[OH:26].[C-:27]#[N:28].[Na+].O>CN1CCCC1=O.C(OCC)(=O)C.[Ni](Br)Br>[OH:26][C:3]1[C:4]2[C:5]([CH3:25])([CH3:24])[CH2:6][C:7]([OH:19])([C:20]([F:23])([F:22])[F:21])[CH:8]([NH:12][C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[C:9]=2[CH:10]=[CH:11][C:2]=1[C:27]#[N:28]

Participants

7

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 87538493HCID 87538493, compound

Product 1

HCID 87539088HCID 87539088, compoundYield 19.3%

Reagents, catalysts & solvents 3

HCID 278492Nickel(II) bromideCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

50 mg of the 2-chloro-8,8-dimethyl-5-(pyridin-3-ylamino)-6-(trifluoromethyl)-5,6,7,8-tetrahydronaphthalene-1,6-diol that is described in Example 159 is dissolved in 0.12 ml of 1-methy-2-pyrrolidinone and mixed with 12.6 mg (0.258 mmol) of sodium cyanide and 28.2 mg (0.129 mmol) of nickel(II) bromide. The reaction mixture is brought to reaction in the microwave as described in the literature (J. Org. Chem. 68, 9122 (2003) (200° C., 20 bar). After cooling, the reaction mixture is diluted with ethyl acetate and then a small amount of water is added. The mixture is filtered over Extrelut (mobile solvent ethyl acetate). The solvent is spun off, and the residue is chromatographed on silica gel (mobile solvent methanol/dichloromethane). 9.4 mg (19.2%) of the desired nitrile is isolated.

Workup

  1. customThe reaction mixture is brought to reaction in the microwave
  2. custom68, 9122 (2003) (200° C., 20 bar)
  3. temperatureAfter cooling
  4. filtrationThe mixture is filtered over Extrelut (mobile solvent ethyl acetate)
  5. customthe residue is chromatographed on silica gel (mobile solvent methanol/dichloromethane)

Sources & evidence

ORD record
ord-3c7e7db080224c6c8dca3edde4b58939
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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