Triethylamine → HCID 178432714, compound

HRID 447189Notes

Reaction equation

HRID 447189 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.I[C:28]1[N:29]=[C:30]([CH3:33])[NH:31][CH:32]=1.C[Si]([C:38]#[C:39][C:40]1[CH:45]=[CH:44][N:43]=[C:42]([C:46]#[N:47])[CH:41]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>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.[Cu]I>[CH3:33][C:30]1[NH:31][CH:32]=[C:28]([C:38]#[C:39][C:40]2[CH:45]=[CH:44][N:43]=[C:42]([C:46]#[N:47])[CH:41]=2)[N:29]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 2724141Tetrabutylammonium FluorideHCID 451164464-[2-(Trimethylsilyl)ethynyl]pyridine-2-carbonitrileHCID 178433060HCID 178433060, compound

Product 1

HCID 178432714HCID 178432714, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Triphenylphosphine (126 mg, 0.48 mmol), bis(triphenylphosphine)palladium(II) chloride (1.01 g, 1.44 mmol) and triethylamine (3.65 g, 101.2 mmol) were dissolved in 40 ml of dry THF. This mixture was evacuated and backfilled with argon several times to remove oxygen from the solution. 4-iodo-2-methyl-1H-imidazole [Tetrahedron Letters 30(11), 1409 (1989)] (5.0 g, 20.8 mmol), 4-trimethylsilanylethynyl-pyridine-2-carbonitrile (4.43 g, 22.1 mmol) and copper (I) iodide (46 mg, 0.24 mmol) were added and the mixture was warmed to 60° C. A 1M solution of tetrabutylammonium fluoride (24 ml, 24.0 mmol) was added dropwise over a period of 30 min. After the addition was finished, the reaction mixture was stirred at 60° C. for another hour. The solvent was evaporated. The residue was taken up in 200 mL water and extracted three times with 200 ml of ethyl acetate. The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (methanol/methylene chloride 5:95). The desired product was obtained as a light yellow solid (1.06 g, 21%). MS: m/e=208.9 (M+).

Workup

  1. customThis mixture was evacuated
  2. customto remove oxygen from the solution
  3. additionAfter the addition
  4. customThe solvent was evaporated
  5. extractionextracted three times with 200 ml of ethyl acetate
  6. dry with materialThe combined organic extracts were dried with magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by flash chromatography on silica gel (methanol/methylene chloride 5:95)

Sources & evidence

ORD record
ord-77bae59feacf44a7af0f7115f6bcc363
Source dataset
uspto-grants-2013_07
Patent number
US08481548B2

Reaction notes

Loading…