Potassium Cyanide → 1-Oxo-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-1H-isoindole-5-carbonitrile

HRID 2427715Notes

Reaction equation

HRID 2427715 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:7](=[O:15])[N:6]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1)[CH2:5]2.[C-:28]#[N:29].[K+]>CN(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:15]=[C:7]1[C:8]2[C:4](=[CH:3][C:2]([C:28]#[N:29])=[CH:10][C:9]=2[C:11]([F:14])([F:12])[F:13])[CH2:5][N:6]1[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][C:24]([F:26])([F:27])[F:25])=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 116829765-Chloro-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one

Product 1

HCID 866356721-Oxo-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-1H-isoindole-5-carbonitrileYield 93.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-chloro-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.123 g, 0.3 mmol), Pd(PPh3)4 (0.035 g, 0.03 mmol), KCN (0.057 g, 0.88 mmol), and KI (0.125 g, 0.75 mmol) in HMPA (3 mL) was stirred at 80° C. for 18 h. Workup and silica gel column chromatography using 2:1 hexanes-ethyl acetate afforded 1-Oxo-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-1H-isoindole-5-carbonitrile (0.112 g, 93%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.39 (s, 2H), 4.72 (s, 2H), 7.22 (d, 2H), 7.37 (d, 2H), 7.89 (s, 1H), 8.06 (s, 1H) GC-MS: m/z 400 (M)+, 379 (M−21)+.

Sources & evidence

ORD record
ord-d030f55334034d5985006e51b124da35
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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