Phenylacetylene → HCID 13412744, compound

HRID 365477Notes

Reaction equation

HRID 365477 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.[C:9]1([C:15]#[CH:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(N(CC)CC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:16]#[C:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 13412744HCID 13412744, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 2-amino-6-bromopyridine (200 mg, 1.16 mmol), 1-phenylacetylene (142 mg, 1.39 mmol), bis(triphenylphosphine) palladium (II) chloride (14 mg, 0.02 mmol), and CuI (2 mg, 0.01 mmol) in 2 mL triethylamine was stirred at 60° C. in a sealed tube for 18 hours. The reaction was cooled and concentrated in vacuo to a dark oil. The oil was purified by gravity column chromatography over silica gel with 2% methanol/chloroform to give the desired product as a brown oil. 400 Mhz H1NMR (CDCl3): 4.57(br s, 2H), 6.49(d, 1H), 6.93(d, 1H), 7.38(m, 3H), 7.41(t, 1H), 7.58(d, 1H).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo to a dark oil
  3. customThe oil was purified by gravity column chromatography over silica gel with 2% methanol/chloroform

Sources & evidence

ORD record
ord-899ff3fe962441bb9f3122682a229c07
Source dataset
uspto-grants-2000_10
Patent number
US06127390

Reaction notes

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