Thieno(2,3-c)pyridine → HCID 22607601, compound

HRID 2307782Notes

Reaction equation

HRID 2307782 reaction equation
[S:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C([Li])CCC.[CH3:15][Sn:16](Cl)([CH3:18])[CH3:17]>C1COCC1>[CH3:15][Sn:16]([CH3:18])([CH3:17])[C:2]1[S:1][C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 9224Thieno(2,3-c)pyridineHCID 14016Trimethyltin chlorideHCID 178418339Butyllithium

Product 1

HCID 22607601HCID 22607601, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of thieno[2,3-c]pyridine (J. Wikel, et al., J. Heterocycl. Chem., 1993, 30, 289) (2.0 g, 14.8 mmol) in THF (50 mL) at −78° C. was treated with n-butyllithium (2.5 M solution in hexane, 7.1 mL, 17.8 mmol), warmed to 0° C., stirred for 15 minutes, cooled to −78° C., treated slowly with trimethyltin chloride (3.54 g, 17.8 mmol) in THF (10 mL), warmed to room temperature for 2 hours, and partitioned between ethyl acetate and brine. The ethyl acetate solution was washed with water, and concentrated. The residue was purified by flash chromatography (10-35% ethyl acetate in hexane) to provide the desired product (3.15 g, 71%). MS (APCI) m/e 298 (M+H)+.

Workup

  1. temperaturecooled to −78° C.
  2. temperaturewarmed to room temperature for 2 hours
  3. custompartitioned between ethyl acetate and brine
  4. washThe ethyl acetate solution was washed with water
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (10-35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d4efeef353bd49d4948b893cf90291fe
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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