HCID 19002930, compound → HCID 19002888, compound
Reaction equation
Cl[C:2]1[O:10][C:9]2[C:4](=[N:5][C:6]([CH3:11])=[CH:7][CH:8]=2)[C:3]=1[Cl:12].C([Li])(C)(C)C>C1COCC1>[Cl:12][C:3]1[C:4]2=[N:5][C:6]([CH3:11])=[CH:7][CH:8]=[C:9]2[O:10][CH:2]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2,3-dichloro-5-methylfuro[3,2-b]pyridine (0.661 g, 3.27 mmol) (Example 12, Step 2) in 16 mL of THF was added a 1.7M solution of t-butyllithium (4.04 mL, 6.87 mmol). After 30 min the solution was quenched at -78° C. with methanol and a solution of NH4C1. The reaction was brought to room temperature and extracted with EtOAc. The organic solvents were evaporated and the title compound was purified by flash chromatography on silica with EtOAc:hexane 1:4 to yield 0.444 g (81%).
Workup
- customAfter 30 min the solution was quenched at -78° C. with methanol
- customwas brought to room temperature
- extractionextracted with EtOAc
- customThe organic solvents were evaporated
- customthe title compound was purified by flash chromatography on silica with EtOAc:hexane 1:4
- customto yield 0.444 g (81%)
Sources & evidence
- ORD record
- ord-06347123ff744e688129a25fe29d93b1
- Source dataset
- uspto-grants-1995_12
- Patent number
- US05472964
Reaction notes
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