Water → HCID 67309639, compound

HRID 2383347Notes

Reaction equation

HRID 2383347 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:20]=[C:19](Br)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=[N:8][C:7]=1[CH3:22])=[O:5])[CH3:2].O.[CH3:24][N:25]1CCCC1=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:20]=[C:19]([C:24]#[N:25])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=[N:8][C:7]=1[CH3:22])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 67309113HCID 67309113, compound

Product 1

HCID 67309639HCID 67309639, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
150 °C

Procedure

A suspension of 2-(4-bromonaphthalene-2-yl)-4-methylthiazole-5-carboxylic acid ethyl ester (0.050 g), zinc cyanide (0.031 g) and tetrakis(triphenylphosphine)palladium (0.015 g) in N-methylpyrrolidone (2 mL) was stirred at 150° C. for 50 minutes using microwave reactor (Biotage). To the reaction mixture was added water (15 mL), and the precipitated solid was collected by filtration, and washed with water and n-hexane to give 2-(4-cyanonaphthalene-2-yl)-4-methylthiazole-5-carboxylic acid ethyl ester (0.042 g).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water and n-hexane

Sources & evidence

ORD record
ord-c0a06d997fbc412ea6fadefed3839776
Source dataset
uspto-grants-2012_09
Patent number
US08263622B2

Reaction notes

Loading…