Triethylamine → HCID 16067786, compound

HRID 868808Notes

Reaction equation

HRID 868808 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[N:6][CH:7]=1.[C:9]1([C:15]#[CH:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>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>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:16]#[C:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 5936905-Bromo-2-iodopyridine

Product 1

HCID 16067786HCID 16067786, compoundYield 78%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
60 °C

Procedure

Bis-(triphenylphosphine)-palladium(II)dichloride (62 mg, 0.088 mmol, 0.05 equiv.) was dissolved in 5 ml THF. (500 mg, 1.76 mmol) 5-Bromo-2-iodopyridine and phenylacetylene (216 mg, 2.11 mmol, 1.2 equiv.) were added at room temperature. Triethylamine (0.74 ml, 5.28 mmol, 3 equiv.) and copper(I)iodide (10 mg, 0.053 mmol, 0.03 equiv.) were added and the mixture was stirred for 16 hours at 60° C. The reaction mixture was evaporated to dryness and loaded directly to a silica gel column. The crude product was purified by flash chromatography on a silica gel column eluting with a heptane:ethyl acetate gradient 100:0 to 90:10. The desired 5-bromo-2-phenylethynyl-pyridine (354 mg, 78% yield) was obtained as a light yellow solid, MS: m/e=258.0/259.9 (M+H+).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customThe crude product was purified by flash chromatography on a silica gel column
  3. washeluting with a heptane

Sources & evidence

ORD record
ord-03f0ac20642649ec86cb63553f89c689
Source dataset
uspto-grants-2015_03
Patent number
US08969338B2

Reaction notes

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