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

HRID 1825111Notes

Reaction equation

HRID 1825111 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 3h, 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) δ 8.61 (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. filtrationThe mixture was filtered
  2. washwashed with CH2Cl2
  3. customwas partitioned between H2O (50 ml) and CH2Cl2 (2×50 ml)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography
  7. washeluting with 30–60% EtOAc in hexane

Sources & evidence

ORD record
ord-52a136269f3d4774990ada3f8fb8021d
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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