Cesium carbonate → HCID 67252195, compound

HRID 2427738Notes

Reaction equation

HRID 2427738 reaction equation
[F:1][C:2]1[C:10]([I:11])=[C:9]2[C:5]([CH2:6][NH:7][C:8]2=[O:12])=[CH:4][CH:3]=1.Br[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]#[N:22].C([O-])([O-])=O.[Cs+].[Cs+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O.CCCCCC.C(OCC)(=O)C>[F:1][C:2]1[C:10]([I:11])=[C:9]2[C:5]([CH2:6][N:7]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]#[N:22])[C:8]2=[O:12])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 2855718-Crown-6HCID 895992-(Bromomethyl)benzonitrileHCID 672519166-Fluoro-2,3-dihydro-7-iodo-1H-isoindol-1-one

Product 1

HCID 67252195HCID 67252195, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6-fluoro-7-iodo-2,3-dihydro-isoindol-1-one (0.070 g, 0.25 mmol), 1-bromomethyl-2-cyano-benzene (0.059 g, 0.3 mmol), Cs2CO3 (0.098 g, 0.3 mmol), and 18-crown-6 (0.007 g, 0.025 for mmol) in acetone (5 mL) was stirred at 70° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 6-fluoro-7-iodo-2-(2-cyano-benzyl)-2,3-dihydro-isoindol-1-one (0.040 g, 41%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.33 (s, 2H), 5.04 (s, 2H), 7.04-7.71 (m, 6H), GC-MS: m/z 392 (M)+.

Sources & evidence

ORD record
ord-cfdf56d1094a42f0a999d59f304524a2
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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