Sodium hydride → HCID 87210765, compound

HRID 1623406Notes

Reaction equation

HRID 1623406 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:4][C:3]=1[Cl:16].[H-].[Na+].CC1C=CC(S(O[CH2:30][CH:31]2[CH2:36][CH2:35][CH2:34][O:33][CH2:32]2)(=O)=O)=CC=1>CN(C=O)C.[NH4+].[Cl-]>[Br:1][C:2]1[N:7]=[C:6]([N:8]([CH2:30][CH:31]2[CH2:36][CH2:35][CH2:34][O:33][CH2:32]2)[C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH:5]=[CH:4][C:3]=1[Cl:16]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 86618913(Oxan-3-yl)methyl 4-methylbenzene-1-sulfonateHCID 86650605HCID 86650605, compound

Product 1

HCID 87210765HCID 87210765, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of tert-butyl 6-bromo-5-chloropyridin-2-ylcarbamate (1.00 g, 3.25 mmol) in DMF (13.0 mL) was added 60% dispersion NaH (0.156 g, 3.90 mmol) under Argon. Stirred at 0° C. for 30 mins then added racemic (tetrahydro-2H-pyran-3-yl)methyl 4-methylbenzenesulfonate (1.143 g, 4.23 mmol). The mixture was then allowed to warm to 25° C. and stirring continued for 19 h. The reaction mixture then was diluted with saturated NH4Cl and then extracted with EtOAc (×3). Organics washed with water (×2), saturated brine (×2), then dried (Na2SO4), filtered and evaporated under reduced pressure. The resulting residue was purified by flash column chromatography (silica gel; 5% to 15% EtOAc/heptanes) to give racemic tert-butyl 6-bromo-5-chloropyridin-2-yl((tetrahydro-2H-pyran-3-yl)methyl)carbamate (938 mg).

Workup

  1. temperatureto warm to 25° C.
  2. stirringstirring
  3. waitcontinued for 19 h
  4. extractionextracted with EtOAc (×3)
  5. washOrganics washed with water (×2), saturated brine (×2)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe resulting residue was purified by flash column chromatography (silica gel; 5% to 15% EtOAc/heptanes)

Sources & evidence

ORD record
ord-9a481f6d6f3144b4ac84adb56d6fd01f
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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