Tributyltin Chloride → HCID 58303321, compound

HRID 246238Notes

Reaction equation

HRID 246238 reaction equation
I[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.C([Mg]Cl)(C)C.[CH2:16]([Sn:20]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])Cl)[CH2:17][CH2:18][CH3:19]>C1COCC1.CCCCCC>[CH2:26]([Sn:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 15096Tributyltin ChlorideHCID 107527743-Iodoimidazo[1,2-a]pyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 58303321HCID 58303321, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
20 °C

Procedure

In a 100 mL three-necked flask, 3-iodoimidazo[1,2-a]pyridine (0.9 g, 3.69 mmol) was dissolved in 50 ml THF at −5° C. using an acetone/ice bath. Isopropylmagnesium chloride (1.3 M, 2.84 ml, 3.69 mmol) was added via a syringe and a light white suspension formed. After 0.5 h, tributylchlorostannane (1.15 g, 0.95 μl, 3.69 mmol) was added. This was stirred at 20° C. for 1.5 h. The reaction mixture was diluted with hexane (100 ml), quenched with a saturated solution of ammonium chloride and the organics were washed with 50% brine/water. The organic layer was dried over sodium sulfate, filtered and concentrated to give 3-tributylstannanyl-imidazo[1,2-a]pyridine as an oil. 1H NMR (300 MHz, CDCl3) δ 8.03 (d, 1H) 7.61 (d, 1H) 7.59 (s, 1H) 7.17 (m, 1H) 6.72 (m, 1H) 0.9-1.55 (m, 27).

Workup

  1. customa light white suspension formed
  2. customquenched with a saturated solution of ammonium chloride
  3. washthe organics were washed with 50% brine/water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6ae8bed5c55343ef82dda9584caca9bb
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…