Phenylacetylene → HCID 67690736, compound

HRID 744118Notes

Reaction equation

HRID 744118 reaction equation
I[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:11][C:12]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:13]=2[C:14]([O:16][CH3:17])=[O:15])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:23]1([C:29]#[CH:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(N(CC)CC)C.O1CCCC1.[Cu]I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:22][C:20]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([NH:11][C:9](=[O:10])[CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:30]#[C:29][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:3]=2)[CH:21]=1

Participants

7

Reactant 2

HCID 10821PhenylacetyleneHCID 53966750HCID 53966750, compound

Product 1

HCID 67690736HCID 67690736, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of methyl 2-(3-iodophenylacetamido)-4-chlorobenzoate (m.p. 100°-101° C.; prepared by the general procedure described above; 860 mg, 2 mmol) in triethylamine (20 ml) and tetrahydrofuran (5 ml), was added copper (I) iodide (5 mg), bis(triphenylphosphine)palladium (II) dichloride (20 mg) and phenylacetylene (0.33 ml, 306 mg, 3 mmol), and the mixture stirred overnight at room temperature and then for 5 h at reflux. The solvents were removed, the residue partitioned between ethyl acetate (30 ml) and aqueous citric acid (10%, 25 ml), and the organic layer washed with water (25 ml) and brine (25 ml). After drying (MgSO4), the solution was evaporated and the residue subjected to chromatography on silica gel (4:1 petrol-ethyl acetate as eluant) to afford methyl 4-chloro-2-(3-phenylethynylphenyl)acetamidobenzoate as a colourless gum (824mg); δH (CDCl3) 3.75 (2H, s, --CH2 --), 3.87 (3H, s, CO2Me), 7.03 (1H, dd, J 9.4 and 2.1 Hz, 5-H), 7.33-7.38 (5H, m, ArH), 7.48-7.55 (4H, m, ArH), 7.91 (1H, d, J 9.4 Hz, 6-H), 8.82 (1H, d, J 2.1 Hz, 3-H), and 11.14 (1H, br s, --NHCO--).

Workup

  1. customprepared by the general procedure
  2. temperaturefor 5 h at reflux
  3. customThe solvents were removed
  4. customthe residue partitioned between ethyl acetate (30 ml) and aqueous citric acid (10%, 25 ml)
  5. washthe organic layer washed with water (25 ml) and brine (25 ml)
  6. dry with materialAfter drying (MgSO4)
  7. customthe solution was evaporated

Sources & evidence

ORD record
ord-e25a9926361942959a2008e307566566
Source dataset
uspto-grants-1996_09
Patent number
US05559125

Reaction notes

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