Potassium Cyanide → HCID 66873196, compound

HRID 2427716Notes

Reaction equation

HRID 2427716 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9](Cl)[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].[K+].CCCCCC.CCOC(C)=O.[CH3:40][N:41](P(N(C)C)(N(C)C)=O)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>[O:12]=[C:7]1[C:8]2[C:9]([C:40]#[N:41])=[CH:10][C:2]([C:25]#[N:26])=[CH:3][C:4]=2[CH2:5][N:6]1[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

Participants

6

Reactant 4

HCID 9032Potassium CyanideHCID 12679HexamethylphosphoramideHCID 117044755-Bromo-7-chloro-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-oneHCID 21226206Ethyl acetate hexane

Product 1

HCID 66873196HCID 66873196, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-7-chloro-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.781, 1.86 mmol), Pd(PPh3)4 (0.635 g, 0.55 mmol), KCN (0.357 g, 5.5 mmol), and KI (0.77 g, 4.65 mmol) in HMPA (8 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 3-Oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-4,6-dicarbonitrile (0.300 g, 44%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.41 (s, 2H), 4.83 (s, 2H), 7.22 (d, 2H), 7.39 (d, 2H), 7.92 (s, 1H), 8.08 (s, 1H) GC-MS: m/z 357 (M)+, 272 (M-85)+.

Sources & evidence

ORD record
ord-5f43986f1bf6447a9a7a1043665625a3
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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