Triethylamine → HCID 178418884, compound

HRID 860137Notes

Reaction equation

HRID 860137 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:35]([C:37]1[N:38]=[C:39]([CH3:50])[N:40](COCC[Si](C)(C)C)[CH:41]=1)#[CH:36]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[CH3:8][C:4]1[CH:3]=[C:2]([C:36]#[C:35][C:37]2[N:38]=[C:39]([CH3:50])[NH:40][CH:41]=2)[CH:7]=[CH:6][N:5]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 27628354-Bromo-2-methylpyridineHCID 58765592HCID 58765592, compound

Product 1

HCID 178418884HCID 178418884, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Bromo-2-methyl-pyridine (1.92 g, 11.2 mmol) was dissolved in 50 mL dry THF and triethylamine (3.9 mL, 30 mmol) was added. This mixture was evacuated and backfilled with argon several times to remove oxygen from the solution. Triphenylphosphin (73 mg, 0.28 mmol) and bis(triphenylphosphin)palladium(II)chloride (327 mg, 0.47 mmol) were added and the reaction mixture was stirred at RT for 20 min. Copper(I)iodide (53 mg, 0.28 mmol) and a mixture of 4-ethynyl-2-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole and 5-ethynyl-2-methyl-1-(2-trimethyl-silanyl-ethoxymethyl)-1H-imidazole (2.2 g, 9.3 mmol) were added. The reaction mixture was then stirred at RT overnight. The solvent was evaporated. The residue was taken up in 50 mL water and extracted three times with ethyl acetate (70 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 80:20 →0:100 gradient ) and the desired compound was obtained as a mixture of 2 isomers (2.86 g, 94%), MS: m/e=327.2 (M+).

Workup

  1. customThis mixture was evacuated
  2. customto remove oxygen from the solution
  3. additionwere added
  4. stirringThe reaction mixture was then stirred at RT overnight
  5. customThe solvent was evaporated
  6. extractionextracted three times with ethyl acetate (70 mL each)
  7. dry with materialThe combined organic extracts were dried with sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 80:20 →0:100 gradient )

Sources & evidence

ORD record
ord-ac78f2c3095a498cbe3bf819f0359677
Source dataset
uspto-grants-2006_12
Patent number
US07153874B2

Reaction notes

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