Sodium hydride → HCID 86762616, compound

HRID 2409043Notes

Reaction equation

HRID 2409043 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[NH:12][CH:11]=[CH:10][C:5]2=[N:6][C:7]=1[C:8]#[N:9].[H-].[Na+].[CH3:15][Si:16]([CH2:19][CH2:20][O:21][CH2:22]Cl)([CH3:18])[CH3:17]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[N:12]([CH2:22][O:21][CH2:20][CH2:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[CH:11]=[CH:10][C:5]2=[N:6][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 86689858HCID 86689858, compound

Product 1

HCID 86762616HCID 86762616, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-fluoro-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile (758 mg, 4.71 mmol) in THF (20 mL) was added NaH (60% in mineral oil, 452 mg, 9.42 mmol). After stirring for 30 min, SEM-Cl (1527 mg, 9.42 mmol) was added, followed by stirring at RT for 16 h. The reaction mixture was quenched by adding sat'd aq.NH4Cl and extracted with EtOAc (100 mL×2). The combined extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with a petroleum ether:EtOAc gradient (10:1-0:10) to afford 1096 mg (80%) of 6-fluoro-1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile. MS (ESI): m/z=292.1[M+1]+.

Workup

  1. stirringby stirring at RT for 16 h
  2. customThe reaction mixture was quenched
  3. additionby adding sat'd aq
  4. extractionNH4Cl and extracted with EtOAc (100 mL×2)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by SiO2 chromatography
  9. washeluting with a petroleum ether

Sources & evidence

ORD record
ord-39e8eb5dfdcb42cea7d76a8e8d3618fe
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

Loading…