Sodium Cyanide → HCID 57949655, compound

HRID 2427713Notes

Reaction equation

HRID 2427713 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9](I)[CH:10]=1)[C:7](=[O:12])[N:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)[CH2:5]2.[C-:25]#[N:26].[Na+]>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[Cl:1][C:2]1[CH:10]=[C:9]([C:25]#[N:26])[C:8]2[C:7](=[O:12])[N:6]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)[CH2:5][C:4]=2[CH:3]=1

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 67252143HCID 67252143, compound

Product 1

HCID 57949655HCID 57949655, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-chloro-7-iodo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.339 g, 0.73 mmol), Pd(PPh3)4 (0.084 g, 0.073 mmol), sodium cyanide (0.046 g, 0.95 mmol), and CuI (0.017 g, 0.073 mmol) in acetonitrile (5 mL) was stirred at 80° C. for 18 h. Workup and silica gel column chromatography using 2:1 hexanes-ethyl acetate afforded 6-chloro-3-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-4-carbonitrile (0.184 g, 69%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.31 (s, 2H), 4.81 (s, 2H), 7.20 (d, 2H), 7.37 (d, 2H), 7.62 (s, 1H), 7.76 (s, 1H). GC-MS: m/z 366 (M)+.

Sources & evidence

ORD record
ord-3531b953831a43f6b6acea4c809bffcc
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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