Sodium Cyanide → HCID 11703499, compound

HRID 2427710Notes

Reaction equation

HRID 2427710 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]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:16][CH:15]=1)[CH2:5]2.[C-:27]#[N:28].[Na+].CCCCCC.CCOC(C)=O>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:27]#[N:28])[C:8]2[C:7](=[O:12])[N:6]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([O:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[CH:18][CH:19]=3)[CH2:5][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 8929Sodium CyanideHCID 21226206Ethyl acetate hexaneHCID 67252565HCID 67252565, compound

Product 1

HCID 11703499HCID 11703499, compoundYield 58%

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-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.675 g, 1.42 mmol), Pd(PPh3)4 (0.162 g, 0.14 mmol), sodium cyanide (0.089 g, 1.85 mmol), and CuI (0.027 g, 0.14 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 (typically 2:1 hexane-EtOAc) afforded 6-chloro-3-oxo-2-(4-phenoxy-benzyl)-2,3-dihydro-1H-isoindole-4-carbonitrile (0.307 g, 58%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.32 (s, 2H), 4.77 (s, 2H), 6.95-7.38 (m, 9H), 7.63 (s, 1H), 7.75 (s, 1H). GC-MS: m/z 374 (M)+, 297 (M−77)+, 281 (M-93)+.

Sources & evidence

ORD record
ord-3280ecdcd59a482ab78fa252bc0f5c88
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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