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

HRID 246643Notes

Reaction equation

HRID 246643 reaction equation
[Cl: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].[NH4+].[Cl-]>O1CCCC1>[Cl: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

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 178418918HCID 178418918, compoundHCID 178477877HCID 178477877, compound

Product 1

HCID 1784482296-chloro-3-(tributylstannyl)-1H-indazoleYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 6-chloro-3-iodo-1H-indazole (337 mg, 1.21 mmol) in dry tetrahydrofuran (20 mL) was added drop-wise isopropylmagnesium chloride (1.33 mL, 2M in THF, 2.66 mmol) at −16° C. under N2 atmosphere. After stirring for 20 minutes, tributylchlorostannane (472 mg, 1.45 mmol) was added drop-wise at −16° C., and then it was warmed to 20° C. for 2 h. Then NH4Cl solution (2 mL) was added and product extracted with dichloromethane (15 mL), organic phase was washed with water (2×20 mL) and brine (2×20 mL). The organic layer was dried over Na2SO4, filtered and concentrated to afford 6-chloro-3-(tributylstannyl)-1H-indazole (413 mg, crude) as yellow oil which was used to next step without further purification.

Workup

  1. extractionproduct extracted with dichloromethane (15 mL), organic phase
  2. washwas washed with water (2×20 mL) and brine (2×20 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7c2d1e5327cb4a3e848a01d9cf4525d5
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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