Sodium hydride → HCID 118523377, compound

HRID 1486946Notes

Reaction equation

HRID 1486946 reaction equation
[H-].[Na+].[N:3]1([CH2:8][CH2:9][CH2:10][OH:11])[CH2:7][CH2:6][CH2:5][CH2:4]1.[Br:12][C:13]1[CH:14]=[CH:15][C:16](F)=[N:17][CH:18]=1>C1COCC1>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([O:11][CH2:10][CH2:9][CH2:8][N:3]2[CH2:7][CH2:6][CH2:5][CH2:4]2)=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2093421-PyrrolidinepropanolHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 118523377HCID 118523377, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.591 g, 14.77 mmol) was added portionwise to a solution, of 3-(pyrrolidin-1-yl)propan-1-ol (1.615 g, 12.50 mmol) in THF (20 mL) at to 0° C. then stirred at ambient temperature for 30 minutes, 5-Bromo-2-fluoropyridine (2 g, 11.36 mmol) was added and the resulting mixture stirred at ambient temperature for 2 h before being quenched by the addition of a sat. aqueous solution of ammonium chloride. The moisture was extracted with EtOAc (2×100 mL), the organic layer dried, over Na2SO4, filtered and evaporated to afford pale yellow solid. The crude product was purified by FCC, elution gradient 0 to 10% MeOH in DCM, to afford the desired material (2.70 g, 83%) as a yellow solid. Mass Spectrum: m/z (ES+)[M+H]+=285.

Workup

  1. stirringthe resulting mixture stirred at ambient temperature for 2 h
  2. custombefore being quenched by the addition of a sat. aqueous solution of ammonium chloride
  3. extractionThe moisture was extracted with EtOAc (2×100 mL)
  4. dry with materialthe organic layer dried, over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto afford pale yellow solid
  8. customThe crude product was purified by FCC, elution gradient 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-c226fdade8ea4b1c9857b1884240e1af
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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