Triethylamine → HCID 101451949, compound

HRID 1048713Notes

Reaction equation

HRID 1048713 reaction equation
I[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[C:16]1([C:22]#[CH:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>CN(C)C=O.[Cu](I)I.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:16]1([C:22]#[C:23][C:2]2[N:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]3=[N:4][C:3]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 10567382Ethyl 3-iodoimidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 101451949HCID 101451949, compoundYield 76.4%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

In a flask placed under an argon flow, 1.82 g (5.77 mmol) of ethyl 3-iodoimidazo[1,2-a]pyridine-2-carboxylate were dissolved in 6 ml of dimethylformamide with magnetic stirring. To this solution were added: 0.11 g (0.577 mmol) of copper iodide, 0.776 ml (6.93 mmol) of phenylacetylene and 6 ml (43 mmol) of triethylamine. The reaction medium was degassed with argon for 10 min before adding 0.529 g (0.577 mmol) of Pd2(dba)3. The mixture was stirred at r.t. for 16 h before being filtered on celite. The celite was washed with 50 ml of ethyl acetate, and then the filtrate was washed with 2×50 ml of water. After separation, the aqueous phase was extracted with 2×50 ml of ethyl acetate; the combined organic phases were washed with 70 ml of a saturated NaCl aqueous solution, dried on Na2SO4 which was then removed by filtration. The obtained filtrate was concentrated in vacuo. The crude residue was purified by flash chromatography on a silica gel cartridge (eluent: heptane/ethyl acetate, 6/4, v/v). 1.28 g (yield=57%) of ethyl 3-(phenylethynyl)imidazo[1,2-a]pyridine-2-carboxylate were obtained as a pale yellow solid. LC-MS: m/z=291 (MH+); UV purity at 254 nm=93%. 1H NMR (300 MHz, DMSO) δ 8.70 (d, J=6.8 Hz, 1H), 7.74 (dd, J=22.1, 6.2 Hz, 3H), 7.53 (dd, J=17.6, 6.9 Hz, 4H), 7.23 (t, J=6.3 Hz, 1H), 4.36 (d, J=4.7 Hz, 2H), 1.36 (d, J=7.1 Hz, 3H).

Workup

  1. customIn a flask placed under an argon
  2. additionTo this solution were added
  3. customThe reaction medium was degassed with argon for 10 min
  4. filtrationbefore being filtered on celite
  5. washThe celite was washed with 50 ml of ethyl acetate
  6. washthe filtrate was washed with 2×50 ml of water
  7. customAfter separation
  8. extractionthe aqueous phase was extracted with 2×50 ml of ethyl acetate
  9. washthe combined organic phases were washed with 70 ml of a saturated NaCl aqueous solution
  10. customdried on Na2SO4 which
  11. customwas then removed by filtration
  12. concentrationThe obtained filtrate was concentrated in vacuo
  13. customThe crude residue was purified by flash chromatography on a silica gel cartridge (eluent: heptane/ethyl acetate, 6/4, v/v)

Sources & evidence

ORD record
ord-9a00a2c63b4f43e996db18edeee67e4f
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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