Phthalimide potassium salt → 3-chloro-5-({6-chloro-3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-2-fluorophenyl}oxy)benzonitrile

HRID 1874785Notes

Reaction equation

HRID 1874785 reaction equation
Br[CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.[K]>CN(C=O)C>[Cl:19][C:17]1[CH:16]=[C:13]([CH:12]=[C:11]([O:10][C:5]2[C:6]([Cl:9])=[CH:7][CH:8]=[C:3]([CH2:2][N:25]3[C:21](=[O:31])[C:22]4[C:23](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:24]3=[O:26])[C:4]=2[F:20])[CH:18]=1)[C:14]#[N:15]

Participants

4

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 594515763-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile

Product 1

HCID 594516123-chloro-5-({6-chloro-3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-2-fluorophenyl}oxy)benzonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (1.8 g, 4.8 mmol) was dissolved in DMF (50 mL) and potassium phthalimide (2.25 g, 12.0 mmol) was added. The reaction mixture was placed in an oil bath at 60° C. and stirred for 2-3 h. The reaction mixture was cooled to RT and the solvent was evaporated. Purification was accomplished by column chromatography (CH2Cl2/MeOH) to afford the title compound (1.9 g, 90%). 1H NMR (400 MHz, DMSO-d6): δ ppm 7.70-7.98 (m, 6H), 7.39-7.49 (m, 2H), 7.35 (dd, 1H), 4.81 (s, 2H). MS: m/z 463.2 (M+23).

Workup

  1. customThe reaction mixture was placed in an oil bath at 60° C.
  2. customthe solvent was evaporated
  3. customPurification

Sources & evidence

ORD record
ord-2896b6b403a142939b2dbad2de56d1a5
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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