Phthalimidine → HCID 57949516, compound

HRID 2427564Notes

Reaction equation

HRID 2427564 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[F:20].C([O-])([O-])=O.[Cs+].[Cs+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O.CCCCCC.C(OCC)(=O)C>[F:20][C:14]1[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=1[CH2:12][N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]1=[O:10]

Participants

8

Reactant 4

HCID 10199PhthalimidineHCID 10796Cesium carbonateHCID 2855718-Crown-6HCID 902971-(Bromomethyl)-2,4-difluorobenzene

Product 1

HCID 57949516HCID 57949516, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,3-dihydro-isoindol-1-one (0.133 g, 1 mmol), 1-bromomethyl-2,4-difluoro-benzene (0.248 g, 1.2 mmol), Cs2CO3 (0.816 g, 2.5 mmol), and 18-crown-6 (0.026 g, 0.11 mmol) in acetone (5 mL) was stirred at 70° C. for 16 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-(2,4-difluoro-benzyl)-2,3-dihydro-isoindol-1-one (0.199 g, 77%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.34 (s, 2H), 4.84 (s, 2H), 6.85 (m, 2H), 7.35-7.54 (m, 4H), 7.86 (d, 1H).

Sources & evidence

ORD record
ord-9ba52b31369b44fbb55b7de8008124b0
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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