Sodium hydride → (R)-2((1-(Benzyloxy)propan-2-yl)oxy)-3-bromopyridine

HRID 1524089Notes

Reaction equation

HRID 1524089 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([OH:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:15][C:16]1[C:17](Cl)=[N:18][CH:19]=[CH:20][CH:21]=1>CN(C=O)C>[CH2:1]([O:8][CH2:9][C@H:10]([O:12][C:17]1[C:16]([Br:15])=[CH:21][CH:20]=[CH:19][N:18]=1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6933243-Bromo-2-chloropyridineHCID 10953891(2R)-1-(benzyloxy)propan-2-ol

Product 1

HCID 90313507(R)-2((1-(Benzyloxy)propan-2-yl)oxy)-3-bromopyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (R)-1-(benzyloxy)propan-2-ol (2.0 g, 12 mmol) in dry DMF (5 mL) was added NaH (1.5 g, 36 mmol) at 0 Celsius. The reaction mixture was then stirred for 30 min before adding 3-bromo-2-chloropyridine (2.3 g, 12 mmol) and stirring continued for another 4 h. The reaction was quenched by slow addition of water (10 mL) and the resultant mixture extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over Na2SO4, filtered, concentrated to dryness, and the crude product purified by FCC to provide the title compound.

Workup

  1. stirringstirring
  2. waitcontinued for another 4 h
  3. customThe reaction was quenched by slow addition of water (10 mL)
  4. extractionthe resultant mixture extracted with ethyl acetate (3×10 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customthe crude product purified by FCC

Sources & evidence

ORD record
ord-a7a9d52943af488786797a4057051757
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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