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

HRID 246361Notes

Reaction equation

HRID 246361 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[N:10]=[C:9]2I.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>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[N:10]=[C:9]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]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 712799945-(3-chlorophenoxy)-3-iodo-1-methyl-1H-indazoleHCID 178418918HCID 178418918, compound

Product 1

HCID 712795465-(3-chlorophenoxy)-1-methyl-3-(tributylstannyl)-1H-indazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-16 °C

Procedure

5-(3-Chlorophenoxy)-3-iodo-1-methyl-1H-indazole (0.154 g, 400 μmol) was dissolved in THF (3.00 mL). The colorless solution was cooled to −16° C. (NaCl/ice bath) then isopropylmagnesium chloride (2M in THF, 224 μL, 448 μmol) was added dropwise at −16° C. The reaction mixture was stirred at −16° C. for 20 min then tributylchlorostannane (150 mg, 125 μL, 460 μmol) was added slowly. The reaction mixture was warmed to 25° C. and stirred for 1.5 h. The reaction mixture was quenched with saturated ammonium chloride solution, extracted with dichloromethane, and the combined organics dried over MgSO4 and concentrated to a yellow oil. The residue was dried under high vacuum to give 5-(3-chlorophenoxy)-1-methyl-3-(tributylstannyl)-1H-indazole. The mass of this material was greater than the theoretical yield of the desired product. The yield was assumed to be quantitative, and the material was used directly in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was warmed to 25° C.
  2. stirringstirred for 1.5 h
  3. customThe reaction mixture was quenched with saturated ammonium chloride solution
  4. extractionextracted with dichloromethane
  5. dry with materialthe combined organics dried over MgSO4
  6. concentrationconcentrated to a yellow oil
  7. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-2a3564e969ae4467827d4312bcf10d4f
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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