Sodium Bicarbonate → HCID 68219039, compound

HRID 241447

Reaction equation

HRID 241447 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[CH:7][C:6]([CH:9]=[O:10])=[CH:5][CH:4]=1.[CH2:13]([Mg]Br)[CH3:14].C([O-])(O)=O.[Na+]>C1COCC1>[F:12][C:2]([F:11])([F:1])[C:3]1[N:8]=[CH:7][C:6]([CH:9]([OH:10])[CH2:13][CH3:14])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 68219039HCID 68219039, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 6-trifluoromethyl-pyridine-3-carboxaldehyde (3.526 g, 20.136 mmol) in THF (50 mL). Add ethylmagnesium bromide (3.0 M in Et2O, 7.38 mL, 22.1 mmol) quickly. Stir 30 minutes. Pour the reaction mixture into a saturated NaHCO3 aqueous solution (100 mL). Extract with EtOAc (3×50 mL). Wash the combined organic extracts with a saturated NaCl aqueous solution (75 mL). Dry the organic extracts over Na2SO4; filter; collect the filtrate; and concentrate the filtrate under reduced pressure. Purify the residue by flash chromatography (Analogix® 40 g @ 40 mL/min) eluting with a gradient of EtOAc/hexanes (5% to 50%) over 30 minutes to give the title compound (2.01 g, 49% yield) as a yellow oil. 1H NMR (400.43 MHz, d6-DMSO) δ 8.66 (d, J=1.6 Hz, 1H), 7.95 (dd, J=1.9, 8.1 Hz, 1H), 7.81 (d, J=8.0 Hz, 1H), 5.47 (d, J=4.5 Hz, 1H), 4.60 (q, J=5.8 Hz, 1H), 1.65-1.59 (m, 2H), 0.79 (t, J=7.4 Hz, 3H).

Workup

  1. extractionExtract with EtOAc (3×50 mL)
  2. washWash the combined organic extracts with a saturated NaCl aqueous solution (75 mL)
  3. dry with materialDry the organic extracts over Na2SO4
  4. filtrationfilter
  5. customcollect the filtrate
  6. concentrationand concentrate the filtrate under reduced pressure
  7. customPurify the residue by flash chromatography (Analogix® 40 g @ 40 mL/min)
  8. washeluting with a gradient of EtOAc/hexanes (5% to 50%) over 30 minutes

Sources & evidence

ORD record
ord-8c8fa22a41c5438c97d12ef1faa9ee45
Source dataset
uspto-grants-2014_02
Patent number
US08648200B2

Linked notes

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