Sodium borohydride → 6-Bromo-2-chloro-3-(difluoromethoxy)pyridin-4-amine

HRID 407218

Reaction equation

HRID 407218 reaction equation
[N:1]([C:4]1[CH:9]=[C:8]([Br:10])[N:7]=[C:6]([Cl:11])[C:5]=1[O:12][CH:13]([F:15])[F:14])=[N+]=[N-].[BH4-].[Na+]>CO>[Br:10][C:8]1[N:7]=[C:6]([Cl:11])[C:5]([O:12][CH:13]([F:15])[F:14])=[C:4]([NH2:1])[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866754034-Azido-6-bromo-2-chloro-3-(difluoromethoxy)pyridine

Product 1

HCID 866754046-Bromo-2-chloro-3-(difluoromethoxy)pyridin-4-amineYield 77.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Azido-6-bromo-2-chloro-3-(difluoromethoxy)pyridine (0.563 g, 1.880 mmol) was then dissolved in CH3OH (15 mL), and NaBH4 (0.107 g, 2.82 mmol) was added. The reaction mixture was stirred at ambient temperature for 15 min at which point thin-layer chromatographic (TLC) analysis indicated complete consumption of starting material. The reaction mixture was concentrated and partitioned between EtOAc and H2O. The organic phase was dried and concentrated. The product was purified by flash chromatography (SiO2, EtOAc/hexane gradient) to yield the title compound as a white solid (0.398 g, 77%): mp 138-140° C.; 1H NMR (600 MHz, DMSO-d6) δ 6.98 (t, J=73.1 Hz, 1H), 6.84 (d, J=14.6 Hz, 2H); EIMS m/z 274.

Workup

  1. customconsumption of starting material
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between EtOAc and H2O
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customThe product was purified by flash chromatography (SiO2, EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-2f0be027e79b4c5b84b5ffdb7dc6833e
Source dataset
uspto-grants-2014_06
Patent number
US08754229B2

Linked notes

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