4-(Tri-n-butylstannyl)pyridine → 7-Chloro-2-pyridin-4-ylthieno[3,2-b]pyridine

HRID 985232Notes

Reaction equation

HRID 985232 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)CCC.[Cl:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]2[CH:27]=[C:28](I)[S:29][C:22]=12>CN(C=O)C>[Cl:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]2[CH:27]=[C:28]([C:6]3[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=3)[S:29][C:22]=12

Participants

4

Reactant 2

HCID 27373184-(Tri-n-butylstannyl)pyridineHCID 177504007-Chloro-2-iodothieno(3,2-b)pyridine

Product 1

HCID 221436777-Chloro-2-pyridin-4-ylthieno[3,2-b]pyridineYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tereakis(triphenylphosphine)palladium (54 mg, 0.05 mmole) was added to a solution of 4-(tributylstannyl)pyridine (0.432 g, 1.17 mmole) and 7-chloro-2-iodothieno[3,2-b]pyridine (0.347 g, 1.17 mmole) in DMF (5 ml). The reaction mixture was stirred at reflux for 3 h, cooled to room temperature. The mixture was filtered, washed with CH2Cl2 and was partitioned between H2O (50 ml) and CH2Cl2 (2×50 ml). The combined organic layers were dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 30-60% EtOAc in hexane to give pale yellow color solid (0.103 g, 36%); 1H NMR (300 MHz, CDCl3) δ8.61 (1H, d, J=5.1 Hz), 7.95 (1H, s), 7.66 (2H, m), 7.44 (2H, m), 7.31 (1H, d, J=5.1 Hz); ESIMS (MH+): 481.10.

Workup

  1. temperatureat reflux for 3 h
  2. filtrationThe mixture was filtered
  3. washwashed with CH2Cl2
  4. customwas partitioned between H2O (50 ml) and CH2Cl2 (2×50 ml)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography
  8. washeluting with 30-60% EtOAc in hexane

Sources & evidence

ORD record
ord-f737e76fbc244e04991fd6172d63bd5a
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

Loading…