Diisopropylethylamine → 2-Bromo-3-methoxy-6-trifluoroacetamidopyridine

HRID 1976046Notes

Reaction equation

HRID 1976046 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([NH2:10])[N:3]=1.C(N(CC)C(C)C)(C)C.C([O:23][C:24](=O)[C:25]([F:28])([F:27])[F:26])(=O)C.C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([NH:10][C:24](=[O:23])[C:25]([F:28])([F:27])[F:26])[N:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 12752924Acetyl trifluoroacetateHCID 127582096-Bromo-5-methoxypyridin-2-amine

Product 1

HCID 215844182-Bromo-3-methoxy-6-trifluoroacetamidopyridineYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Bromo-3-methoxy-6-aminopyridine (Desc. 6; 1.0 g, 4.9 mmol) in dichloromethane (25 ml) was treated with N,N-diisopropylethylamine (2.2 ml, 12.3 mmol) and the solution cooled to 0° C. Trifluoroacetic acetic anhydride (770 μl, 5.4 mmol) was then added dropwise and the solution stirred to 22° C. over 2 hours. The mixture was then poured into saturated sodium bicarbonate solution (25 ml) and extracted with dichloromethane (25 ml). The extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by flash silica chromatography to give the product as a white solid (890 mg, 3.0 mmol, 61% yield).

Workup

  1. extractionextracted with dichloromethane (25 ml)
  2. dry with materialThe extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash silica chromatography

Sources & evidence

ORD record
ord-d84292f3518846eeb53849cb2d558ac9
Source dataset
uspto-grants-2001_05
Patent number
US06225320B1

Reaction notes

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