Tributyltin Chloride → 5-(tert-butyldimethylsilyloxy)-1-methyl-3-(tributylstannyl)-1H-indazole

HRID 245953Notes

Reaction equation

HRID 245953 reaction equation
[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[N:11]=[C:10]2I)([CH3:4])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[CH2:25]([Sn:29]([CH2:35][CH2:36][CH2:37][CH3:38])([CH2:31][CH2:32][CH2:33][CH3:34])Cl)[CH2:26][CH2:27][CH3:28]>C1COCC1>[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[N:11]=[C:10]2[Sn:29]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:25][CH2:26][CH2:27][CH3:28])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 712798665-((tert-Butyldimethylsilyl)oxy)-3-iodo-1-methyl-1H-indazoleHCID 178418918HCID 178418918, compound

Product 1

HCID 712796055-(tert-butyldimethylsilyloxy)-1-methyl-3-(tributylstannyl)-1H-indazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-16 °C

Procedure

In a round-bottomed flask, 5-(tert-butyl-dimethyl-silanyloxy)-3-iodo-1-methyl-1H-indazole (140 mg, 0.36 mmol) was dissolved in THF (2 ml). The solution was cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride (2.0 M in THF, 0.22 ml, 0.44 mmol) was added dropwise. The reaction mixture was stirred at −16° C. for 20 min then tributylchlorostannane (0.11 ml, 0.41 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature over 1.5 h then quenched with saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to provide 5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-tributylstannanyl-1H-indazole as a light yellow oil which was used without further purification.

Workup

  1. additionwas added dropwise
  2. temperatureto warm to room temperature over 1.5 h
  3. customthen quenched with saturated aqueous NH4Cl
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialthen dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dd8b89f4a9534fd6a6f03935e122a7cd
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…