tert-Butanol → 2-[(2-{2-[Isopropyl(methyl)amino]ethoxy}pyridin-3-yl)oxy]ethanol
Reaction equation
Cl[C:2]1[C:7]([O:8][CH2:9][CH2:10][O:11]C2CCCCO2)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:18][N:19]([CH2:23][CH2:24][OH:25])[CH:20]([CH3:22])[CH3:21].CC(C)([O-])C.[K+].C(O)(C)(C)C>C1(C)C=CC=CC=1>[CH:20]([N:19]([CH3:18])[CH2:23][CH2:24][O:25][C:2]1[C:7]([O:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=[CH:4][N:3]=1)([CH3:22])[CH3:21]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of 2-chloro-3-[2-(tetrahydro-2H-pyran-2-yloxy]ethoxy]pyridine (from Example 4; 100 mg, 0.39 mmol), 2-(N-methyl-N-isopropylamino)ethanol (68 μl, 0.58 mmol) and 1.0 M potassium tert-butoxide in tert-butanol (0.8 mL, 0.80 mmol) in 4 mL of toluene was heated at 100° C. for 1 day. The organic phase was washed with 3×2 mL of water and 2 mL of brine. The organic phase was shaken at 50° C. with 4 mL of 2.0 M acetic acid for 2 days. The aqueous phase was washed with 3×3 mL of ethyl acetate, made basic by addition of potassium hydroxide, saturated with sodium chloride and extracted with 3×2 mL of ethyl acetate. The organic phase was dried (MgSO4) and concentrated under reduced pressure to give 75 mg (0.30 mmol, 76%) of the title compound as a colorless oil. LC-UV purity 95%. MS m/z 255 (M+1)+, calc. 255 (M+1)+.
Workup
- washThe organic phase was washed with 3×2 mL of water and 2 mL of brine
- washThe aqueous phase was washed with 3×3 mL of ethyl acetate
- additionmade basic by addition of potassium hydroxide, saturated with sodium chloride
- extractionextracted with 3×2 mL of ethyl acetate
- dry with materialThe organic phase was dried (MgSO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-527679e07f49435eb1fec9404f6f7480
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07226925B2
Reaction notes
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