Potassium Carbonate → HCID 86660280, compound

HRID 1631033Notes

Reaction equation

HRID 1631033 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1.Cl.[C:12]([O:16][C:17](=[O:21])[CH2:18][NH:19][CH3:20])([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH2:2][N:19]([CH3:20])[CH2:18][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:21])=[N:4][CH:5]=1)#[N:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11252350Sarcosine t-butyl ester hydrochlorideHCID 219277766-(Bromomethyl)pyridine-3-carbonitrile

Product 1

HCID 86660280HCID 86660280, compoundYield 117.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-bromomethylnicotinonitrile (Advanced Chemical Intermediates, 1.39 g; 7.06 mmol), sarcosine tert-butyl ester hydrochloride (1.54 g; 8.47 mmol) and K2CO3 (2.34 g; 17.0 mmol) in MeCN (25 mL) heated at 60° C. for 18 hours. The solvent was evaporated in vacuo. The residue was dissolved in a mixture of DCM and water and then poured through a hydrophobic frit. The filtrate was evaporated to afford the title product (2.17 g, quantitative). 1H NMR (CDCl3, 400 MHz) δ 8.82 (1 H, d, J=2 Hz), 7.95-7.92 (1 H, dd, J=8.4, 2 Hz), 7.73 (1 H, d, J=8 Hz), 3.91 (2 H, s), 3.28 (2 H, s), 2.41 (3 H, s), 1.48 (9 H, s).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in a mixture of DCM and water
  3. additionpoured through a hydrophobic frit
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-e79df6a4d62e44c9b059a4df64a68ebc
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

Loading…