Tributylstannane → HCID 86669799, compound

HRID 1615538Notes

Reaction equation

HRID 1615538 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[CH2:19]([SnH:23]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH3:22]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[C:8](/[Sn:23]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:9]\[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 5948TributylstannaneHCID 68191113HCID 68191113, compound

Product 1

HCID 86669799HCID 86669799, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl [3-(4-chlorophenyl)prop-2-yn-1-yl]carbamate (5.97 g, 22.5 mmol) in THF (240 mL) under an atmosphere of argon was added bis(triphenylphosphine)palladium(II) chloride (0.788 g, 1.12 mmol) and tri-n-butyltin hydride (9.55 mL, 35.5 mmol). The solution was stirred at room temperature for 90 minutes. The solvent was evaporated and the residue was purified using column chromatography on silica gel (220 g Analogix column, gradient hexane to 20% EA in hexane over 30 minutes) to give the product (11.2 g, 90%). LCMS: (AA) ES+ 556, 558. 1H NMR (400 MHz, d6-DMSO) δ: 7.37-7.31 (m, 2H), 6.96 (m, 2H), 5.83-5.60 (m, 1H), 3.60-3.37 (m, 2H), 1.44-1.36 (m, 6H), 1.34 (m, 9H), 1.26-1.15 (m, 6H), 0.89-0.77 (m, 15H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified
  3. customon silica gel (220 g Analogix column, gradient hexane to 20% EA in hexane over 30 minutes)

Sources & evidence

ORD record
ord-964a0370a6fe47328cf19634ea43d21e
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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