Sodium hydride → N-Methoxy-N-methyl-1-Triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

HRID 2365424Notes

Reaction equation

HRID 2365424 reaction equation
[CH3:1][O:2][N:3]([CH3:15])[C:4]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=[O:5].[H-].[Na+].[CH:18]([Si:21](Cl)([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19]>CN(C=O)C>[CH3:1][O:2][N:3]([CH3:15])[C:4]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]([Si:21]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:18]([CH3:20])[CH3:19])[CH:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 86707830N-Methoxy-N-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

Product 1

HCID 86707831N-Methoxy-N-methyl-1-Triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamideYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-Methoxy-N-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide (300 mg, 1.46 mmol) in DMF (5 mL) was cooled to in an ice bath and sodium hydride (73 mg of 60% dispersion, 1.83 mmol) added in one portion. The mixture was stirred for 5 minutes then triisopropylsilyl chloride (353 mg, 1.83 mmol) added dropwise. The reaction was then stirred for 14 hrs during which time the temperature reached rt. The reaction was then quenched by pouring into a mixture of ice and 25% ammonium chloride solution (50 mL). The resulting mixture was then extracted with EtOAc (2×20 mL) and the combined extracts washed with water (10 mL) and brine (10 mL) then dried over magnesium sulfate. Subsequent filtration and concentration afforded a yellow oil. This crude oil was considered sufficiently pure to carry forward directly. Yield=92%

Workup

  1. stirringThe reaction was then stirred for 14 hrs during which time the temperature
  2. customreached rt
  3. customThe reaction was then quenched
  4. additionby pouring into a mixture of ice and 25% ammonium chloride solution (50 mL)
  5. extractionThe resulting mixture was then extracted with EtOAc (2×20 mL)
  6. washthe combined extracts washed with water (10 mL) and brine (10 mL)
  7. dry with materialthen dried over magnesium sulfate
  8. filtrationSubsequent filtration and concentration
  9. customafforded a yellow oil

Sources & evidence

ORD record
ord-801008e347fe4fa0b8e78380aa40c7ea
Source dataset
uspto-grants-2014_04
Patent number
US08697697B2

Reaction notes

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