Tributyltin Chloride → 6-Fluoro-1-tributylstannyl-imidazo[1,5-a]pyridine

HRID 246549Notes

Reaction equation

HRID 246549 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][C:10]=2I)[CH:7]=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:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][C:10]=2[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])[CH:7]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 712798256-Fluoro-1-iodoimidazo[1,5-A]pyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 712799216-Fluoro-1-tributylstannyl-imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −16° C. solution of 6-fluoro-1-iodoimidazo[1,5-a]pyridine (158 mg, 603 μmol) in THF (4.64 mL) was added isopropylmagnesium chloride (368 μL, 736 μmol) dropwise. After 20 min tributylchlorostannane (232 mg, 193 μL, 712 μmol) was added dropwise at −16° C. and allowed to warm to room temperature. After 2 h the reaction was quenched with saturated ammonium chloride and diluted with ethyl acetate. The phases were separated and the organic phase washed with brine. The organic layer was collected, concentrated in vacuo, and used in the next step without further purification.

Workup

  1. customAfter 2 h the reaction was quenched with saturated ammonium chloride
  2. additiondiluted with ethyl acetate
  3. customThe phases were separated
  4. washthe organic phase washed with brine
  5. customThe organic layer was collected
  6. concentrationconcentrated in vacuo
  7. customused in the next step without further purification

Sources & evidence

ORD record
ord-f52b80281417489eafd43aa4da27b664
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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