Sodium Bicarbonate → 6-Chloro-4-iodopyridin-3-amine

HRID 513087Notes

Reaction equation

HRID 513087 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8]C(=O)OC(C)(C)C)=[C:4]([I:16])[CH:3]=1.C([O-])(O)=O.[Na+]>Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([I:16])[CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 53415320tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate

Product 1

HCID 184070406-Chloro-4-iodopyridin-3-amineYield 93%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The solution of tert-butyl 6-chloro-4-iodopyridin-3-ylcarbamate (10.0 g, 28 mmol) in 3M HCl (600 mL) was heated at 60° C. for 12 h. The mixture was allowed to cool to room temperature and treated with sat. NaHCO3 to pH=8. The aqueous layer was extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, concentrated and purified by chromatography on silica gel (10% ethyl acetate in petroleum ether as eluant) to afford 6-chloro-4-iodopyridin-3-amine (6.6 g, 93%). 1H-NMR (CDCl3, 400 MHz) δ 7.81 (s, 1H), 7.60 (s, 1H), 4.13 (br s, 2H).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (100 mL×3)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. custompurified by chromatography on silica gel (10% ethyl acetate in petroleum ether as eluant)

Sources & evidence

ORD record
ord-95beda0c52984ab9b3d05f678e6f3748
Source dataset
uspto-grants-2015_08
Patent number
US09102672B2

Reaction notes

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