Trimethyltin chloride → HCID 22000199, compound

HRID 1976069Notes

Reaction equation

HRID 1976069 reaction equation
C([Li])(C)(C)C.[CH3:6][O:7][C:8]1[CH:9]=[N:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=1.[CH3:18][Sn:19](Cl)([CH3:21])[CH3:20]>O1CCCC1>[CH3:6][O:7][C:8]1[C:9]([Sn:19]([CH3:21])([CH3:20])[CH3:18])=[N:10][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 220001965-Methoxy-2-(trifluoromethyl)pyridineHCID 178418306HCID 178418306, compound

Product 1

HCID 22000199HCID 22000199, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of t-butyllithium (1.7M in pentane; 8.5 ml, 14.45 mmol) was added dropwise to a stirred solution of 3-methoxy-6-trifluoromethylpyridine (1.57 g, 8.87 mmol) in dry tetrahydrofuran (20 ml) at −78° C. over 5 min. After stirring for 10 min at −78° C. a solution of trimethyltin chloride in tetrahydrofuran (18 ml, 1 M in THF, 18 mmol) was added over 5 min. The reaction mixture was allowed to warm up to room temperature over 5 hour and then quenched with water (50 ml) and extraxted with hexane (3×30 ml). The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (100 g, hexane:diethyl ether 0-10%) to afford 3-methoxy-6-trifluoromethyl-2-trimethystannylpyridine (0.7 g, 23%) H1 NMR δ(250 MHz, CDCl3): 7.50 (1H, d, J 8.7 Hz), 7.02 (1H, d, J 8.7 Hz), 3.85 (3H, s), 0.35 (9H, s); and afford 3-methoxy-6-trifluoromethyl-4-trimethylstannylpyridine (1.7 g, 57%) H1 NMR δ(250 MHz, CDCl3): 8.38 (1H, s), 7.65 (1H, s), 3.95 (3H, s) 0.35 (9H, s).

Workup

  1. additionwas added over 5 min
  2. customquenched with water (50 ml) and extraxted with hexane (3×30 ml)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (100 g, hexane:diethyl ether 0-10%)

Sources & evidence

ORD record
ord-7b2373d8bc5c4b668bbdc6f68c0a087d
Source dataset
uspto-grants-2001_05
Patent number
US06225320B1

Reaction notes

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