Tributyltin Chloride → 1-Tributylstannyl-imidazo[1,5-a]pyridine

HRID 246346Notes

Reaction equation

HRID 246346 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12.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>[CH2:26]([Sn:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[N:3]=[CH:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12)[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 71279920HCID 71279920, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 712798061-Tributylstannyl-imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 1-iodo-imidazo[1,5-a]pyridine (150 mg, 0.62 mmol) in THF (3 mL) at −10° C. (ice/acetone) was added isopropylmagnesium chloride (2.0 M in THF, 37 mL, 0.74 mmol). The reaction mixture was stirred at −10° C. for 20 min then tributylchlorostannane (0.20 mL, 0.74 mmol) was added. The reaction was stirred at −10° C. for 30 min then warmed to room temperature and stirred for 1 h. The reaction was quenched with water and extracted with EtOAc (2×). The combined organics were dried over MgSO4 and concentrated to afford 1-tributylstannanyl-imidazo[1,5-a]pyridine as a yellow oil which was used without further purification.

Workup

  1. stirringThe reaction was stirred at −10° C. for 30 min
  2. temperaturethen warmed to room temperature
  3. stirringstirred for 1 h
  4. customThe reaction was quenched with water
  5. extractionextracted with EtOAc (2×)
  6. dry with materialThe combined organics were dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-99964a2fb75e460da6614b54eb8f3e0a
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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