Triethylamine → HCID 86688172, compound

HRID 708329Notes

Reaction equation

HRID 708329 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH3:9].C(N(CC)CC)C.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19]>C1COCC1.[Cu](I)I>[CH3:9][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:3]=1[C:22]#[C:21][Si:18]([CH3:20])([CH3:19])[CH3:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 189587744-Bromo-3-methylpyridine--hydrogen chloride (1/1)

Product 1

HCID 86688172HCID 86688172, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-bromo-3-methyl pyridine hydrochloride (5.0 g, 24.0 mmol) in THF (degassed, 80 mL) was added copper iodide (450 mg, 2.40 mmol) and triethylamine (20.0 mL, 143.9 mmol). After degassing for 15 min, palladium tetrakis triphenylphosphine (830 mg, 0.72 mmol) and trimethylsilylacetylene (6.10 mL, 43.16 mmol) were added. The mixture was heated at 50° C. for 16 h then cooled to rt and filtered. The crude residue was purified via silica gel chromatography (EtOAc-Hexanes, 10%) to afford the title compound (3.95 g, 87%) as clear but dark oil.

Workup

  1. customAfter degassing for 15 min
  2. temperaturethen cooled to rt
  3. filtrationfiltered
  4. customThe crude residue was purified via silica gel chromatography (EtOAc-Hexanes, 10%)

Sources & evidence

ORD record
ord-33071a8eadb744209d29f50913ff3a3b
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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