Tributylstannane → HCID 19007555, compound

HRID 2377757Notes

Reaction equation

HRID 2377757 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:2].[CH2:9]([SnH:13]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH3:12].CC(N=NC(C#N)(C)C)(C#N)C>C1COCC1>[CH2:18]([Sn:13]([CH2:9][CH2:10][CH2:11][CH3:12])([CH2:14][CH2:15][CH2:16][CH3:17])/[CH:2]=[CH:1]/[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 1860033-Ethynylpyridine

Product 1

HCID 19007555HCID 19007555, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Ethynyl-pyridine (1.03 g, 10 mmol) and tributyltin hydride (3.2 mL, 12 mmol) were stirred in dry THF (10 mL) with a catalytic amount of AIBN at 50° C. for 18 h. The solution was concentrated in vacuo and purified by silica gel chromatography (10% EOAc/hexanes) to give 2.09 g (53%) of the title compound as a clear oil. 1H NMR (400 MHz, DMSO-d6): δ 8.61 (s, 1H), 8.45 (d, 1H, J=3.2 Hz), 7.75 (d, 1H, J=7.6 Hz), 7.25-7.29 (m, 1H), 6.93 (AB q, 2H, J=57.2, 19.6 Hz), 1.49-1.59 (m, 6H), 1.28-1.39 (m, 6H), 0.87-1.00 (m, 15H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompurified by silica gel chromatography (10% EOAc/hexanes)

Sources & evidence

ORD record
ord-21797869669c4b7c91ad02dfc67a85ed
Source dataset
uspto-grants-2008_12
Patent number
US07470700B2

Reaction notes

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