Tributyltin Chloride → HCID 71279802, compound

HRID 246416Notes

Reaction equation

HRID 246416 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH:19]([F:21])[F:20])=[CH:15][CH:16]=2)[C:11](I)=[N:10]1.C([Mg]Cl)(C)C.[CH2:28]([Sn:32]([CH2:38][CH2:39][CH2:40][CH3:41])([CH2:34][CH2:35][CH2:36][CH3:37])Cl)[CH2:29][CH2:30][CH3:31]>C1COCC1>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH:19]([F:21])[F:20])=[CH:15][CH:16]=2)[C:11]([Sn:32]([CH2:34][CH2:35][CH2:36][CH3:37])([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:28][CH2:29][CH2:30][CH3:31])=[N:10]1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 71279676HCID 71279676, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 71279802HCID 71279802, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-16 °C

Procedure

1-(2-(1,3-dioxan-2-yl)ethyl)-5-(difluoromethoxy)-3-iodo-1H-indazole (242 mg, 571 mmol) was dissolved in THF (3.00 mL). The colorless solution was cooled to −16° C. (NaCl/ice bath), isopropylmagnesium chloride 2M in THF (319 μL, 639 μmol) was added dropwise at −16° C. The reaction mixture was stirred at −16° C. for 20 min. Then, tributylchlorostannane (214 mg, 178 μL, 656 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 (3×30 mL), organics dried over MgSO4 and concentrated to a yellow oil. The residue was dried under high vacuum and taken into next step without further purification yielding 1-(2-(1,3-dioxan-2-yl)ethyl)-5-(difluoromethoxy)-3-(tributylstannyl)-1H-indazole, assumed quantitative and used into the next step without further purification.

Workup

  1. additionwas added dropwise at −16° C
  2. temperatureThe reaction mixture was warmed to 25° C.
  3. stirringstirred for 1.5 h
  4. customThe reaction mixture was quenched with saturated ammonium chloride solution
  5. extractionextracted with dichloromethane (3×30 mL)
  6. dry with materialorganics dried over MgSO4
  7. concentrationconcentrated to a yellow oil
  8. customThe residue was dried under high vacuum
  9. customtaken into next step without further purification

Sources & evidence

ORD record
ord-b36f467b4853439ca4b39174495d2671
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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