Sodium hydride → 1-(2-butylsulfanyl-pyrimidin-4-yl)-4-methoxy-1H-indole-3-carboxylic acid amide

HRID 1947061Notes

Reaction equation

HRID 1947061 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[C:7]([C:14]([NH2:16])=[O:15])=[CH:8][NH:9]2.[CH2:17]([S:21][C:22]1[N:27]=[C:26](Cl)[CH:25]=[CH:24][N:23]=1)[CH2:18][CH2:19][CH3:20]>CN(C=O)C>[CH2:17]([S:21][C:22]1[N:23]=[C:24]([N:9]2[C:10]3[C:6](=[C:5]([O:4][CH3:3])[CH:13]=[CH:12][CH:11]=3)[C:7]([C:14]([NH2:16])=[O:15])=[CH:8]2)[CH:25]=[CH:26][N:27]=1)[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 597434972-Butylsulfanyl-4-chloro-pyrimidineHCID 693120594-methoxy-1H-indole-3-carboxylic acid amide

Product 1

HCID 693120521-(2-butylsulfanyl-pyrimidin-4-yl)-4-methoxy-1H-indole-3-carboxylic acid amideYield 98.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH (397 mg, 9.94 mmol, 60% dispersion) was added to a solution of 4-methoxy-1H-indole-3-carboxylic acid amide (1.575 g, 8.28 mmol) in dry DMF (5 mL) at 0° C., stirred for 20 min, and a solution of 2-butylsulfanyl-4-chloro-pyrimidine (1.846 g, 9.108 mmol) in DMF (4 mL) added at 0° C. The mixture was allowed to warm up to RT without stirring, whereupon a solid precipitated. Dry THF (20 mL) was added, and the mixture stirred overnight. Water was added to the mixture, and the resulting white solid was filtered off, washed with water (20 mL) and DCM (20 mL), and air-dried for 3 h to provide 1-(2-butylsulfanyl-pyrimidin-4-yl)-4-methoxy-1H-indole-3-carboxylic acid amide (2.916 g, 98.8% yield) as a crude solid.

Workup

  1. stirringwithout stirring, whereupon a solid
  2. customprecipitated
  3. additionDry THF (20 mL) was added
  4. stirringthe mixture stirred overnight
  5. additionWater was added to the mixture
  6. filtrationthe resulting white solid was filtered off
  7. washwashed with water (20 mL) and DCM (20 mL)
  8. customair-dried for 3 h

Sources & evidence

ORD record
ord-cb27d6c27cf24460823bab34cc9bc0f2
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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