Triethylamine → HCID 22677634, compound

HRID 1837945Notes

Reaction equation

HRID 1837945 reaction equation
[CH3:1][N:2]([C:9](=[O:12])[C:10]#[CH:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].I[C:14]1[CH:15]=[C:16]([O:20][CH3:21])[CH:17]=[CH:18][CH:19]=1.CCN(CC)CC.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O.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>[CH3:21][O:20][C:16]1[CH:15]=[C:14]([C:11]#[C:10][C:9]([N:2]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:1])=[O:12])[CH:19]=[CH:18][CH:17]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 69839Benzene, 1-iodo-3-methoxy-HCID 45082712HCID 45082712, compound

Product 1

HCID 22677634HCID 22677634, compoundYield 35%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-(N-methylprop-2-ynoylamino)acetate (312 mg, 1.84 mmol) in THF (6 mL) was added 3-iodoanisole (475 mg, 0.24 mL, 2.03 mmol), dichlorobis(triphenylphosphine)palladium(II) (133 mg, 0.19 mmol), copper(I) iodide (36 mg, 0.19 mmol) and Et3N (279 mg, 0.39 mL, 2.76 mmol). The resulting mixture was stirred in dark for 2 h. A saturated NH4Cl solution (30 mL) was then added and the mixture was extracted with EtOAc (2×30 mL). The combined organic layers were washed with a saturated NaCl solution (60 mL), dried (Na2SO4) and concentrated under reduced pressure to give a dark oil, which was dissolved in EtOAc and filtered through a pad of silica gel. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography (33% EtOAc/hex) to give ethyl 2-[3-(3-methoxyphenyl)-N-methylprop-2-ynoylamino]acetate (175 mg, 35%) as a light yellow oil: 1H NMR (CDCl3; a mixture of two rotomers) δ 1.30 (t, J=7.0 Hz, 3H), 3.10 (1.35H), 3.36 (s, 1.65H), 3.81 (s, 1.35H), 3.82 (s, 1.65H), 4.20-4.30 (m, 3.2H), 4.39 (s, 0.8H), 6.97-7.29 (m, 4H); HPLC ES-MS m/z (rel abundance) 276 (MH+, 100%).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×30 mL)
  2. washThe combined organic layers were washed with a saturated NaCl solution (60 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give a dark oil, which
  6. filtrationfiltered through a pad of silica gel
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by flash chromatography (33% EtOAc/hex)

Sources & evidence

ORD record
ord-397c82565da74fb1aa41cbc37e1095a0
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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