Methanol--water (1/1) → Thienopyridine

HRID 1639663Notes

Reaction equation

HRID 1639663 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.[Li]CCCC.CO.O>C1COCC1>[S:10]1[C:3]2[C:4](=[N:5][CH:6]=[CH:7][CH:2]=2)[CH:8]=[CH:9]1

Participants

5

Reactant 3

HCID 22242641Methanol--water (1/1)HCID 667211077-Bromothieno[3,2-b]pyridineHCID 178418339Butyllithium

Product 1

HCID 12210218ThienopyridineYield 62.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Dissolve 7-bromo-thieno[3,2-b]pyridine (3.69 g, 17 mmol) in dry THF (20 mL) and cool to −78° C. Add n-BuLi (1.6 M in hexane, 21.2 mL, 34 mmol) slowly to the mixture at −78° C. and stir at −78° C. for 20 min. Add MeOH/H2O=1/1 (20 mL) and stir at room temperature for 1 h. Extract the reaction mixture with CH2Cl2. Wash the organic portion with saturated NaCl solution, dry over Na2SO4, and evaporate. Purify the resulting residue using silica gel chromatography, eluting with 100% hexane to hexane:ethyl acetate=10:1 to give the title compound (1.44 g, 62%). ES/MS m/z 136 (M+1)+.

Workup

  1. extractionExtract the reaction mixture with CH2Cl2
  2. washWash the organic portion with saturated NaCl solution
  3. dry with materialdry over Na2SO4
  4. customevaporate
  5. customPurify the resulting residue
  6. washeluting with 100% hexane to hexane

Sources & evidence

ORD record
ord-7d64c04a6be74722bb1da391b25f1729
Source dataset
uspto-grants-2012_02
Patent number
US08110580B2

Reaction notes

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