Potassium Carbonate → 3-chloro-5-({2-chloro-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}oxy)benzonitrile

HRID 1874763Notes

Reaction equation

HRID 1874763 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14](O)=[O:15])=[O:11])=[CH:4][C:3]=1[OH:21].[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[C:29](F)[CH:30]=1)[C:26]#[N:27].C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([O:21][C:3]2[CH:4]=[C:5]([CH2:8][N:9]3[C:10](=[O:11])[C:12]4[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:14]3=[O:15])[CH:6]=[CH:7][C:2]=2[Cl:1])[CH:30]=1)[C:26]#[N:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27348413-Chloro-5-fluorobenzonitrileHCID 594516542-({[(4-Chloro-3-hydroxyphenyl)methyl]amino}carbonyl)benzoic acid

Product 1

HCID 594515253-chloro-5-({2-chloro-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}oxy)benzonitrileYield 24%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3-Chloro-5-({2-chloro-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}oxy)benzonitrile was prepared in a in a similar manner as described herein from 2-({[(4-chloro-3-hydroxyphenyl)methyl]amino}carbonyl)benzoic acid (3.0 g, 10.4 mmol), 3-chloro-5-fluorobenzonitrile (2.5 g, 15.6 mmol), K2CO3 (4.3 g, 31.0 mmol) and NMP (25.0 mL). Purification was accomplished by column chromatography (hexane/EtOAc) to afford the title compound (1.0 g, 24%) as a solid.

Workup

  1. custom3-Chloro-5-({2-chloro-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}oxy)benzonitrile was prepared in a in a similar manner
  2. customPurification

Sources & evidence

ORD record
ord-4786c67f275f40f2898fad10597d561b
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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