1,2-Dibromoethane → Methyl 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:16][CH2:17]Br.CCOC(C)=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:9]([O:11][CH3:12])=[O:10])[CH2:17][CH2:16]2)[CH:5]=[N:6][CH:7]=1Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a solution of methyl 2-(5-bromopyridin-3-yl)acetate (4.8 g, 20.86 mmol) in DMF (100 mL) was added 60% NaH in mineral oil (1.1 g, 45.9 mmol), and the mixture was stirred at 0° C. for 15 min. A solution of 1,2-dibromoethane (3.92 g, 20.86 mmol) in DMF (20 mL) was added and the mixture was stirred at room temperature for 1 h. Two other portions of 60% NaH in mineral oil (200 and 450 mg) were added sequentially, until conversion was complete. The mixture was poured into EtOAc (1 L) and washed with water (60 mL), dried over Na2SO4 and concentrated in vacuo to give an oil which was used in next step without further purification.
Workup
- stirringthe mixture was stirred at room temperature for 1 h
- washwashed with water (60 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customto give an oil which
- customwas used in next step without further purification
Sources & evidence
- ORD record
- ord-7a451c2992fc4fb0a7e89f88ca5fc476
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08519142B2
Reaction notes
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