Dimethylformamide → HCID 178519658, compound

HRID 2078394Notes

Reaction equation

HRID 2078394 reaction equation
[H-].[Na+].Br[C:4]1[C:5]([OH:11])=[N:6][CH:7]=[C:8]([Cl:10])[CH:9]=1.[H][H].C([Li])(C)(C)C.CN([CH:22]=[O:23])C>C1COCC1>[Cl:10][C:8]1[CH:9]=[C:4]([CH:22]=[O:23])[C:5]([OH:11])=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 178418306HCID 178418306, compoundHCID 178418361HCID 178418361, compoundHCID 178517755HCID 178517755, compound

Product 1

HCID 178519658HCID 178519658, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of NaH (0.22 g, 60% dispersion in oil, 5.5 mmol) in anhydrous THF (20 mL) under argon atmosphere was added 3-bromo-5-chloro-pyridin-2-ol (1.03 g, 5 mmol) in a portionwise manner. After hydrogen evolution had ceased the mixture was cooled to −78° C. and tert-butyl lithium (10 mmol) was added at such a rate that the temperature did not rise above −65° C. The mixture was stirred for 5 mins then DMF (15 mmol) was added keeping the temperature below −50° C. The mixture was allowed to warm to room temperature and partitioned between ethyl acetate and 1N HCl. The organic layer was separated, washed with saturated NaCl, dried over anhydrous Na2SO4, filtered and concentrated to give the title compound (300 mg).

Workup

  1. customdid not rise above −65° C
  2. customthe temperature below −50° C
  3. temperatureto warm to room temperature
  4. custompartitioned between ethyl acetate and 1N HCl
  5. customThe organic layer was separated
  6. washwashed with saturated NaCl
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e2e95b8c6aa94bcca9f39962cc2dcc00
Source dataset
uspto-grants-2011_04
Patent number
US07928233B2

Reaction notes

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