2-Bromopyridine → 2-(Tributylstannyl)pyridine
Reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[Sn:13](Cl)([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH3:17]>CCOC(C)=O>[CH2:22]([Sn:13]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:18][CH2:19][CH2:20][CH3:21])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[CH2:23][CH2:24][CH3:25]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
n-BuLi (200 mL, 0.5 mol) was added dropwise to 2-bromopyridine (79 g, 0.5 mol) under N2 with continuous stirring at −78° C. This solution was stirred at −78° C. for 1 h and (Bu)3SnCl (178.8 g, 0.55 mol) was added dropwise to the reaction solution. After addition, the reaction solution was stirred at −78° C. for 1 h and room temperature for 1 h. TLC (petroleum:EtOAc=10:1) indicated the reaction was complete. The reaction solution was quenched with sat. NH4Cl and extracted with EtOAc (350 mL×3). The combined extracts were washed with water, dried over Na2SO4, concentrated and purified by chromatography, eluted with (petroleum:EtOAc=10:1) to give title compound (110 g, 60%) as a yellow liquid.
Workup
- stirringThis solution was stirred at −78° C. for 1 h
- additionAfter addition
- stirringthe reaction solution was stirred at −78° C. for 1 h and room temperature for 1 h
- customThe reaction solution was quenched with sat. NH4Cl
- extractionextracted with EtOAc (350 mL×3)
- washThe combined extracts were washed with water
- dry with materialdried over Na2SO4
- concentrationconcentrated
- custompurified by chromatography
- washeluted with (petroleum:EtOAc=10:1)
Sources & evidence
- ORD record
- ord-c498f37daced40428fa4a3039d7e9a53
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09056865B2
Reaction notes
Loading…