Hexane → Thienopyridine

HRID 226060Notes

Reaction equation

HRID 226060 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.CCCCCC.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

6

Reactant 4

HCID 8058HexaneHCID 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

3.69 g of 7-Bromo-thieno[3,2-b]pyridine (17 mmol) is dissolved in 20 ml of dry THF and cooled to −78° C. 21.2 ml of n-BuLi 1.6M in hexane (34 mmol) is added slowly to the mixture at −78° C. and stirred at −78° C. for 20 min, and 20 ml of MeOH/H2O=1/1 is added and stirred at room temperature for 1 h. The reaction mixture is extracted with CHCl2. The separated CH2Cl2 layer is washed with sat. NaCl, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane→Hexane:AcOEt=−10:1) to give 1.44 g of the title compound. Yield 62%. mass spectrum (m/e): 136 (M+1); 1H-NMR (CDCl3): 8.73 (m, 1H), 8.22 (m, 1H), 7.79 (m, 1H), 7.61 (m, 1H), 7.29 (m, 1H) ppm.

Workup

  1. stirringstirred at room temperature for 1 h
  2. extractionThe reaction mixture is extracted with CHCl2
  3. washThe separated CH2Cl2 layer is washed with sat. NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-3aed987b86f44710aa2c3b672a17072d
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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