Triethylamine → HCID 67294165, compound

HRID 517958Notes

Reaction equation

HRID 517958 reaction equation
[NH:1]1[CH2:4][CH:3]([CH2:5][CH2:6][OH:7])[CH2:2]1.F[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1.C(N(CC)CC)C>CO>[CH3:15][C:11]1[N:10]=[C:9]([N:1]2[CH2:4][CH:3]([CH2:5][CH2:6][OH:7])[CH2:2]2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 960902-Fluoro-6-methylpyridineHCID 198883912-(Azetidin-3-yl)ethanol

Product 1

HCID 67294165HCID 67294165, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

2-(Azetidin-3-yl)ethanol (4.91 mmol, 0.497 g), 2-fluoro-6-methylpyridine (9.83 mmol, 1.014 ml, 1.092 g), and triethylamine (14.74 mmol, 2.072 ml, 1.492 g) were dissolved in MeOH (2 ml). The solution was then heated (microwave) to 150° C. for 1 hour. Solvent was removed under reduced pressure. The resulting oil was redissolved in DCM and washed once with water. Solution was dried (Na2SO4), and solvent removed under reduced pressure to give a crude product. This was then purified by flash chromatography (10 g silica column, DCM to 2% MeOH in DCM gradient). Appropriate fractions were combined and solvent removed under reduced pressure to give final product. 1H NMR (CDCl3) δ: 7.32 (t, 1H), 6.43 (d, 1H), 6.08 (d, 1H), 4.13 (t, 2H), 3.69 (m, 4H), 2.84 (m, 1H), 2.39 (s, 3H), 1.92 (q, 2H).

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionThe resulting oil was redissolved in DCM
  3. washwashed once with water
  4. dry with materialSolution was dried (Na2SO4), and solvent
  5. customremoved under reduced pressure
  6. customto give a crude product
  7. customThis was then purified by flash chromatography (10 g silica column, DCM to 2% MeOH in DCM gradient)
  8. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-b250d59e947243409ee26c40ee967fce
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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