Tributyltin Chloride → HCID 21253184, compound

HRID 1530885Notes

Reaction equation

HRID 1530885 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][CH:7]=[CH:6][N:5]2[C:17]=1[CH3:18].C([Li])(C)(C)C.[CH2:24]([Sn:28](Cl)([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH3:27]>C(OCC)C.CCCCC>[CH2:33]([Sn:28]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:29][CH2:30][CH2:31][CH3:32])[C:8]1[CH:7]=[CH:6][N:5]2[C:17]([CH3:18])=[C:2]([CH3:1])[N:3]=[C:4]2[C:9]=1[NH:10][C:11](=[O:16])[C:12]([CH3:14])([CH3:15])[CH3:13])[CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 3

HCID 15096Tributyltin ChlorideHCID 21873970HCID 21873970, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 21253184HCID 21253184, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Procedure

A solution of 1 g of 2,3-dimethyl-8-pivaloylaminoimidazo[1,2-a]pyridine in 40 ml of diethyl ether is treated dropwise at −78° C. with 8 ml of a 1.5 molar solution of t-butyllithium in n-pentane. The mixture is stirred for 15 min and then treated with 3.3 ml of tri-n-butyltin chloride. The internal temperature is then allowed to rise to room temperature, the mixture is poured onto ice water and extracted three times with ethyl acetate, the combined extracts are washed with a little water and dried over potassium carbonate, the solvent is stripped off in vacuo and the oil obtained is chromatographed on silica gel using ethyl acetate/petroleum ether (1:3) as an eluent. 1.3 g of 7-tributylstannyl-2,3-dimethyl-8-pivaloylaminoimidazo[1,2-a]pyridine are obtained as a viscous oil.

Workup

  1. customto rise to room temperature
  2. additionthe mixture is poured onto ice water
  3. extractionextracted three times with ethyl acetate
  4. washthe combined extracts are washed with a little water
  5. dry with materialdried over potassium carbonate
  6. customthe oil obtained
  7. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-7576916a31b34f98bc6d5db9635e170e
Source dataset
uspto-grants-2001_03
Patent number
US06197783B1

Reaction notes

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