Dimethylformamide → HCID 57949706, compound

HRID 2427714Notes

Reaction equation

HRID 2427714 reaction equation
[F:1][C:2]1[C:10](I)=[C:9]2[C:5]([CH2:6][N:7]([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)[C:8]2=[O:12])=[CH:4][CH:3]=1.[CH3:25][N:26](C=O)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[C-]#N.[Zn+2].[C-]#N.[Zn]>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][N:7]([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)[C:8](=[O:12])[C:9]=2[C:10]=1[C:25]#[N:26]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 67250154HCID 67250154, compound

Product 1

HCID 57949706HCID 57949706, compoundYield 19%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 6-fluoro-7-iodo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-one (0.100 g, 0.22 mmol), PdCl2(dppf)2 (0.008 g, 0.011 mmol), zinc cyanide (0.051 g, 0.44 mmol), and zinc (0.007 g, 0.011 mmol) in DMF (5 mL) was stirred at 80° C. for 18 h. Workup and silica gel column chromatography using 2:1 hexanes-ethyl acetate afforded 5-fluoro-3-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-4-carbonitrile (0.015 g, 19%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.31 (s, 2H), 4.81 (s, 2H), 7.19 (d, 2H), 7.37 (m, 3H), 7.64 (m, 1H). GC-MS: m/z 350 (M)+.

Sources & evidence

ORD record
ord-980c205505094568a1effeb4b8a530b1
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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