Pyridine → t-Butyl 2-(4-bromobutyramido)-6-methoxypyridine-4-carboxylate

HRID 1612467Notes

Reaction equation

HRID 1612467 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:5]=[C:4]([O:15][CH3:16])[N:3]=1.N1C=CC=CC=1.[Br:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28]>ClCCl.C(OCC)(=O)C>[Br:23][CH2:24][CH2:25][CH2:26][C:27]([NH:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH:5]=[C:4]([O:15][CH3:16])[N:3]=1)=[O:28]

Participants

6

Reactant 3

HCID 1049PyridineHCID 702254-Bromobutyryl chlorideHCID 22252993t-Butyl 2-amino-6-methoxypyridine-4-carboxylate

Product 1

HCID 22253030t-Butyl 2-(4-bromobutyramido)-6-methoxypyridine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of t-butyl 2-amino-6-methoxypyridine-4-carboxylate (D55) (0.263 g) and pyridine (0.12 mL) in dichloromethane (16 mL) under argon, was added 4-bromobutyryl chloride (0.17 mL) dropwise (syringe). The reaction was stirred at room temp for 2.5 h and then diluted with ethyl acetate. The mixture was washed with citric acid solution (10% aq.) and the aqueous layer was re-extracted with ethyl acetate. The combined extracts were washed with aq. bicarbonate, water and brine, dried (MgSO4) and evaporated to give the title compound (D56) as a pale yellow gum (0.47 g).

Workup

  1. washThe mixture was washed with citric acid solution (10% aq.)
  2. extractionthe aqueous layer was re-extracted with ethyl acetate
  3. washThe combined extracts were washed with aq. bicarbonate, water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d5a506df8e284a1d85144cc549e248a0
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

Loading…