Cyclopentanol → 2-Bromo-6-(cyclopentyloxy)pyridine
Reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Na].[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[N:10]=1.[H-].[Na+]>C1COCC1.CCOC(C)=O>[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[N:10]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To cyclopentanol (1 mL), was added sodium (36 mg, 1.56 mmol). When the sodium was consumed, the mixture was diluted with 1 mL THF and 2,6-dibromopyridine (250 mg, 1.06 mmol). The mixture was stirred at 90° C. for 3 h, sodium hydride (20 mg) was added and the mixture was stirred an additional 1 h at 90° C. The reaction was diluted with EtOAc. The organic phase was washed with water (2×) and brine, dried (Na2SO4) and concentrated. The crude material was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient) to afford 222 mg of 159.1 as a colorless oil. LCMS (2 min gradient) RT=2.01 min, 242.15 (M+H)+.
Workup
- customWhen the sodium was consumed
- stirringthe mixture was stirred an additional 1 h at 90° C
- washThe organic phase was washed with water (2×) and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe crude material was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient)
Sources & evidence
- ORD record
- ord-2b3544275d3f4284af0ed004e931cc0a
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576098B2
Reaction notes
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