Tributyltin Chloride → 7-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridine

HRID 418568

Reaction equation

HRID 418568 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.[CH2:11]([Sn:15](Cl)([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([Sn:15]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:11][CH2:12][CH2:13][CH3:14])[S:10][C:3]=12

Participants

5

Reactant 2

HCID 15096Tributyltin ChlorideHCID 112752517-Chlorothieno[3,2-b]pyridine

Product 1

HCID 575166587-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridineYield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-chlorothiene[3,2-b]pyridine 2 (9.82 g, 57.89 mmol) in THF (290 mL) BuLi (2.5 N, 25 mL) was added at −78° C. and the mixture stirred for 20 min at the same temperature. Tributyltin chloride (63.68 mmol, 17.3 mL) was added dropwise and the mixture stirred for 2 h at −78° C. The homogeneous mixture thus obtained was poured in water (200 mL) and extracted with EtOAc (2×200 mL). The organic phase was collected, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (eluent EtOAc/Hex 1:4) to afford 7-chloro-2-(tributylstannyl)thieno[3,2-b]pyridine (6, 24.79 g, 93% yield) as a syrup. MS (m/z): cluster of signals centered around 460.1 (M+1).

Workup

  1. stirringthe mixture stirred for 2 h at −78° C
  2. customThe homogeneous mixture thus obtained
  3. extractionextracted with EtOAc (2×200 mL)
  4. customThe organic phase was collected
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (eluent EtOAc/Hex 1:4)

Sources & evidence

ORD record
ord-82f2a286255d4945891de1e8af9e804b
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Linked notes

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