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

HRID 246636Notes

Reaction equation

HRID 246636 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=2)[N:4]([CH3:15])[N:3]=1.C([Mg]Cl)(C)C.[CH2:21]([Sn:25]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])Cl)[CH2:22][CH2:23][CH3:24]>C1COCC1>[CH3:15][N:4]1[C:5]2[C:10](=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=2)[C:2]([Sn:25]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:21][CH2:22][CH2:23][CH3:24])=[N:3]1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 712801053-iodo-1-methyl-5-(trifluoromethyl)-1H-indazoleHCID 178418918HCID 178418918, compound

Product 1

HCID 712795411-methyl-3-(tributylstannyl)-5-(trifluoromethyl)-1H-indazoleYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-iodo-1-methyl-5-(trifluoromethyl)-1H-indazole (400 mg, 1.2 mmol) in dry THF (15 mL) was added isopropylmagnesium chloride (0.7 mL, 1.3 mmol, 2 M in THF) drop-wise at −16° C. under nitrogen atmosphere, stirred for 30 minutes, then tributylchlorostannane (0.4 mL, 1.3 mmol) was added drop-wise at −16° C. under nitrogen, the reaction mixture was warmed to room temperature slowly and stirred for 2 hours, then quenched with a solution of saturated NH4Cl (40 mL) and product extracted with EtOAc (3×30 mL) then dried over Na2SO4, filtered and concentrated, under reduced pressure to give 1-methyl-3-(tributylstannyl)-5-(trifluoromethyl)-1H-indazole (500 mg, crude) as an oil which was used directly to next step without any further purification.

Workup

  1. stirringstirred for 2 hours
  2. customquenched with a solution of saturated NH4Cl (40 mL) and product
  3. extractionextracted with EtOAc (3×30 mL)
  4. dry with materialthen dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated, under reduced pressure

Sources & evidence

ORD record
ord-5bfe02e00c1b41829a47a74a941b7742
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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