Sodium hydride → HCID 49758976, compound

HRID 877932Notes

Reaction equation

HRID 877932 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:13][C:14]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])[CH3:15].[Cl-].[NH4+]>C1COCC1>[C:14]([Si:17]([CH3:19])([CH3:18])[N:8]1[C:5]2=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]2[CH:10]=[CH:9]1)([CH3:16])([CH3:15])[CH3:13]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 49758976HCID 49758976, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a sealed tube equipped with a septa under nitrogen was added 42 (600 mg, 0.00396 mol) and 20 mL of dry THF and the solution cooled to 0° C. NaH (110 mg, 0.00435 mol) was added portionwise and after 15 min. of stirring at 0° C., TBSCl (656 mg, 0.00435 mol) was added. The septa was replaced by a Teflon screw cap and the sealed tube heated at 80° C. for 3 h. Cooled and neutralized with ammonium chloride solution and extracted with hexanes. The organic phase was dried and concentrated in vacuo to an oil that was subjected to a short plug filtration (10% EtOAC-90% hexanes) to give 871 mg (82%) of compound 43. 1H NMR (500 MHz, CDCl3) 8.2 (s, 1H), 7.8 (s, 1H), 7.25 (s, 1H), 6.4 (s, 1H), 0.9 (s, 9H), 0.6 (s, 6H).

Workup

  1. customIn a sealed tube equipped with a septa under nitrogen
  2. customscrew cap
  3. temperaturethe sealed tube heated at 80° C. for 3 h
  4. temperatureCooled
  5. extractionextracted with hexanes
  6. customThe organic phase was dried
  7. concentrationconcentrated in vacuo to an oil that
  8. filtrationwas subjected to a short plug filtration (10% EtOAC-90% hexanes)

Sources & evidence

ORD record
ord-e7b5b299d92b4fb4a4b178e1184f71af
Source dataset
uspto-grants-2015_03
Patent number
US08987454B2

Reaction notes

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