Water → HCID 21696665, compound

HRID 378797Notes

Reaction equation

HRID 378797 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:3]=1.[N-:16]=[N+]=[N-].[Na+].O.[BH4-].[Na+]>CN(C=O)C.CO>[NH2:16][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:3]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 33557Sodium AzideHCID 4311764Sodium borohydrideHCID 21696617HCID 21696617, compound

Product 1

HCID 21696665HCID 21696665, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 4-chloro-6-trifluoromethylpyridine-2-carboxylate (2.44 g, 10.2 mmol) in aqueous DMF was added NaN3 (0.7 g, 10.8 mmol). The resulting mixture was heated at 70° C. for 18 hr, added to H2O and extracted (3×) with Et2O. The organic layer was concentrated to yield a white solid that was dissolved in 10 mL of MeOH. Excess NaBH4 was added and the reaction mixture stirred at RT for 0.5 hr. This material was added to H2O, extracted (3×) with Et2O. The extract was dried over MgSO4 and concentrated. The resulting residue was purified via flash column chromatography to give 0.95 of product as a white solid; mp 114° C.

Workup

  1. extractionextracted (3×) with Et2O
  2. concentrationThe organic layer was concentrated
  3. customto yield a white solid
  4. extractionextracted (3×) with Et2O
  5. dry with materialThe extract was dried over MgSO4
  6. concentrationconcentrated
  7. customThe resulting residue was purified via flash column chromatography
  8. customto give 0.95 of product as a white solid

Sources & evidence

ORD record
ord-7216734850524731a226917c9e0fc1ff
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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