HCID 19002930, compound → HCID 19002888, compound

HRID 2259508Notes

Reaction equation

HRID 2259508 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]=1

Participants

4

Reactant 2

HCID 19002930HCID 19002930, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 19002888HCID 19002888, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customAfter 30 min the solution was quenched at -78° C. with methanol
  2. customwas brought to room temperature
  3. extractionextracted with EtOAc
  4. customThe organic solvents were evaporated
  5. customthe title compound was purified by flash chromatography on silica with EtOAc:hexane 1:4
  6. 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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