Potassium Cyanide → 2-(5-(3-Amino-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-1-yl)-2-methoxy-3-methylphenyl) acetonitrile

HRID 1662266Notes

Reaction equation

HRID 1662266 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:12]2([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]4[CH:30]=[N:31][CH:32]=[N:33][CH:34]=4)[CH:24]=3)[C:20]3[C:15](=[C:16]([F:21])[CH:17]=[CH:18][CH:19]=3)[C:14]([NH2:22])=[N:13]2)[CH:6]=[C:7]([CH3:11])[C:8]=1[O:9][CH3:10].[C-:35]#[N:36].[K+]>CC#N>[NH2:22][C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[C:12]([C:5]2[CH:6]=[C:7]([CH3:11])[C:8]([O:9][CH3:10])=[C:3]([CH2:2][C:35]#[N:36])[CH:4]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]3[CH:30]=[N:31][CH:32]=[N:33][CH:34]=3)[CH:24]=2)[N:13]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 585794761-(3-(Bromomethyl)-4-methoxy-5-methylphenyl)-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine

Product 1

HCID 585794892-(5-(3-Amino-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-1-yl)-2-methoxy-3-methylphenyl) acetonitrileYield 13.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(3-(bromomethyl)-4-methoxy-5-methylphenyl)-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine (185 mg, 0.36 mmol) in MeCN (5 mL) was added potassium cyanide (69.8 mg, 1.07 mmol) and the reaction mixture was stirred at rt over night. The mixture was filtered and the filtrate was concentrated in vacuo and purified by preparative HPLC to give 23 mg (12%) of the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f308fd3e6e104544a3f7728addb9a94f
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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