Tert-butyl 2,2,2-trichloroethanimidate → 6-({5-Chloro-2-[(1,1-dimethylethyl)oxy]phenyl}methyl)-2-pyridine-carboxylic acid

HRID 2356637Notes

Reaction equation

HRID 2356637 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1.ClC(Cl)(Cl)C(=N)O[C:23]([CH3:26])([CH3:25])[CH3:24]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 684564716-[(5-Chloro-2-hydroxyphenyl)methyl]-2-pyridinecarboxylic acid

Product 1

HCID 117167306-({5-Chloro-2-[(1,1-dimethylethyl)oxy]phenyl}methyl)-2-pyridine-carboxylic acidYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution/suspension of 6-[(5-chloro-2-hydroxyphenyl)methyl]-2-pyridine-carboxylic acid (308 mg) in dry dichloromethane (12 ml) was added t-butyl 2,2,2-trichloroacetimidate (1.67 ml) and boron trifluoride-diethyl etherate (0.05 ml) and the mixture stirred under argon at ambient temperature for 44 hours. Dichloromethane (15 ml) was added and the mixture washed with saturated sodium bicarbonate solution (15 ml). The aqueous layer was extracted with dichloromethane (2×15 ml) and the combined organic extracts washed with brine (25 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by mass-directed autopreparation to afford the title compound (91 mg, 24%) as a white solid.

Workup

  1. washthe mixture washed with saturated sodium bicarbonate solution (15 ml)
  2. extractionThe aqueous layer was extracted with dichloromethane (2×15 ml)
  3. washthe combined organic extracts washed with brine (25 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by mass-directed autopreparation

Sources & evidence

ORD record
ord-f2ccbdd318aa4ffaaf83d4f73eb17e12
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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