Methanol → HCID 67294252, compound

HRID 517957Notes

Reaction equation

HRID 517957 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]=[CH:11][N:10]=1.C(N(CC)CC)C.CO>C(Cl)Cl>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:1]1[CH2:4][CH:3]([CH2:5][CH2:6][OH:7])[CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 97462-FluoropyridineHCID 198883912-(Azetidin-3-yl)ethanol

Product 1

HCID 67294252HCID 67294252, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

2-(Azetidin-3-yl)ethanol (4.92 mmol, 0.498 g), 2-fluoropyridine (9.85 mmol, 0.846 ml, 0.956 g), triethylamine (14.77 mmol, 2.053 ml, 1.495 g) and methanol (2.5 ml) were combined and heated to 150° C. in a microwave for 40 minutes. TLC analysis showed some starting material remained and therefore the solution was heated for a further 40 minutes. The resulting solution was dissolved in DCM (c. 20 ml) and washed with water. Solvent was removed under reduced pressure to yield a crude product. This was then purified by flash chromatography (10 g silica column, DCM to 3% MeOH in DCM gradient). Appropriate fractions were combined and solvent removed under reduced pressure to give final product. 1H NMR (CDCl3) δ: 8.17 (d, 1H), 7.42 (t, 1H), 6.57 (t, 1H), 6.26 (d, 1H), 4.16 (t, 2H), 3.70 (m, 4H), 2.88 (m, 1H), 1.95 (q, 2H).

Workup

  1. temperaturethe solution was heated for a further 40 minutes
  2. washwashed with water
  3. customSolvent was removed under reduced pressure
  4. customto yield a crude product
  5. customThis was then purified by flash chromatography (10 g silica column, DCM to 3% MeOH in DCM gradient)
  6. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-d819ea22f3834c97af800a58fb039ca2
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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