Tributyltin Chloride → HCID 131735986, compound

HRID 2209275Notes

Reaction equation

HRID 2209275 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Li]CCCC.[Sn:26](Cl)([CH2:35][CH2:36][CH2:37][CH3:38])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30]>C1COCC1.CCCCCC>[CH2:35]([Sn:26]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)[CH2:36][CH2:37][CH3:38]

Participants

6

Reactant 3

HCID 15096Tributyltin ChlorideHCID 11530243Tert-butyl 4-(6-bromopyridin-3-yl)piperazine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 131735986HCID 131735986, compoundYield 21.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Into the solution of tert-butyl 4-(6-bromopyridin-3-yl)piperazine-1-carboxylate 7.13 (1.65 g, 4.8 mmol) in THF (30 mL) was added 1M solution of n-BuLi in hexane (5 mL) and n-Bu3SnCl (1.66 g, 5.1 mmol) at −70° C. After 30 min., the reaction was warmed up to rt. After stirring for 1 h., the reaction mixture was extracted with ethyl acetate and washed with brine. After drying with MgSO4, the organic solvent was removed under vaco., the residue was purified by silica gel chromatography to obtain 0.58 g of tert-butyl 4-(6-(tributylstannyl)pyridin-3-yl)piperazine-1-carboxylate 7.14. LCMS [M+H]+: 554.07.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialAfter drying with MgSO4
  4. customthe organic solvent was removed under vaco
  5. custom, the residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-dfec8a7e058748ef9f62653aff75f5bf
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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