Trifluoroacetic acid → (6-methyl-2-pyridinyl)acetic acid TFA salt

HRID 1910060Notes

Reaction equation

HRID 1910060 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([O:11]C(C)(C)C)=[O:10])[CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.[C:23]([OH:29])([C:25]([F:28])([F:27])[F:26])=[O:24]>ClCCl>[OH:29][C:23]([C:25]([F:28])([F:27])[F:26])=[O:24].[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59341204Tert-butyl 2-(6-methylpyridin-2-yl)acetate

Product 1

HCID 66823699(6-methyl-2-pyridinyl)acetic acid TFA saltYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl (6-methyl-2-pyridinyl)acetate (711 mg, 3.43 mmol), triethylsilane (1.370 mL, 8.58 mmol) in Dichloromethane (DCM) (10 mL) was added TFA (3.44 mL, 44.6 mmol) dropwise via syringe. The reaction was stirred for overnight at room temperature. LCMS indicated good conversion, so the reaction was concentrated to a colourless oil, and diethyl ether (6 mL) was added. A white precipitate formed which was collected by filtration, dried at the pump for 10 mins, then under high-vacuum to afford (6-methyl-2-pyridinyl)acetic acid TFA salt (771 mg) as a white solid. LC-MS (ES) m/z=152 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.62 (s, 3H), 3.95 (s, 2H), 7.54 (d, J=7.33 Hz, 2H), 8.11 (br. s., 1H).

Workup

  1. concentrationso the reaction was concentrated to a colourless oil, and diethyl ether (6 mL)
  2. additionwas added
  3. customA white precipitate formed which
  4. filtrationwas collected by filtration
  5. customdried at the pump for 10 mins

Sources & evidence

ORD record
ord-a6615cdb13364fe48a28fcdd62d3eb1d
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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