Tributyltin Chloride → 6-fluoro-3-(tributylstannyl)-1H-indazole

HRID 246633

Reaction equation

HRID 246633 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](I)=[N:7][NH:8]2)=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[CH2:17]([Sn:21]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])Cl)[CH2:18][CH2:19][CH3:20]>C1COCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([Sn:21]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:17][CH2:18][CH2:19][CH3:20])=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 178418918HCID 178418918, compoundHCID 178505447HCID 178505447, compound

Product 1

HCID 1784482326-fluoro-3-(tributylstannyl)-1H-indazoleYield 106.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

6-Fluoro-3-iodo-1H-indazole (300 mg, 1.1 mmol) in 30 mL of dry THF was cooled to −20° C. under nitrogen atmosphere, then isopropylmagnesium chloride (1.2 mL, 2.42 mmol) was added and mixture stirred for 15 mins at −20° C. Tributylchlorostannane (0.4 mL, 1.32 mmol) was added and the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The reaction was quenched with saturated ammonium chloride, product extracted with ethyl acetate (3×50 mL), dried with sodium sulphate, filtered and concentrated to give 6-fluoro-3-(tributylstannyl)-1H-indazole (500 mg, crude) as a colorless oil which was used directly in the next step without further purification.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 1 h
  3. customThe reaction was quenched with saturated ammonium chloride, product
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialdried with sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-29cd64a8d8eb4cdda7c870258d170685
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Linked notes

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