N-(4-iodophenyl)acetamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-Iodo-aniline (15 g, 69 mmol) in dry CH2Cl2 (100 ml) was added acetic anhydride(14.09 g, 138 mmol) at room temperature, the reaction mixture was then stirred for 2 hr. The gray color precipitate formed during the reaction was filtered, washed with ether and collected, the mother solution was concentrated to dryness and AcOEt was added, the resulting precipitate was filtered, washed with ether and combined with the previous solid as the desired product (15.95 g, 88.7%). The gray color precipitate formed during the reaction was filtered washed with ether collected the mother solution was concentrated to dryness and AcOEt was added the resulting precipitate was filtered washed with ether

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-(3-ethoxy-4-methoxy-phenyl)-acrylonitrile (0.7 g, 3.2 mmol), N-(4-iodo-phenyl)-acetamide (1.4 g, 5.4 mmol), NaHCO3 (1.1 g, 12.8 mmol), Bu4NBr (1.2 g, 3.6 mmol) and Pd(OAc)2 (0.04 g, 0.2 mmol) in DMF (15 mL) was heated at 70° C. for 2 days. The cooled mixture was poured into water (150 mL) and was extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water (2×50 mL), brine (50 mL) and dried (MgSO4). Solvent was removed and the residue was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 9:1) to afford N-{4-[2-cyano-1-(3-ethoxy-4-methoxy-phenyl)-vinyl]-phenyl}acetamide (0.4 g, 32%): mp 175-177° C.; 1H NMR (CDCl3) δ 7.51(d, J=8 Hz, 2H), 7.41 (s, 1H), 7.26 (d, J=9.0 Hz, 2H), 7.02-6.89 (m, 3H), 5.57 (s, 1H), 4.11-4.03 (q, J=7 Hz, 2H), 3.92 (s, 3H), 2.19 (s, 3H), 1.44 (t, J=7 Hz, 3H); 13C NMR (CDCl3) δ 168.38, 162.14, 150.93, 147.96, 139.91, 134.84, 129.58, 129.30, 123.08, 119.34, 118.53, 114.06, 111.01, 92.49, 64.53, 55.96, 24.65, 14.66; Anal Calcd for C20H20N2O3: C, 71.46; H, 5.99; N, 8.33. Found: C, 71.46, 6.01; N, 8.25. was extracted with EtOAc (3×50 mL) The combined organic extracts were washed with water (2×50 mL), brine (50 mL) dried (MgSO4) Solvent was removed the residue was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 9:1)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-(3-ethoxy-4-methoxy-phenyl)-acrylonitrile (0.7 g, 3.2 mmol), N-(4-iodo-phenyl)-acetamide (1.4 g, 5.4 mmol), NaHCO3 (1.1 g, 12.8 mmol), Bu4NBr (1.2 g, 3.6 mmol) and Pd(OAc)2 (0.04 g, 0.2 mmol) in DMF (15 mL) was heated at 70° C. for 2 days. The cooled mixture was poured into water (150 mL) and was extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water (2×50 mL), brine (50 mL) and dried (MgSO4). Solvent was removed and the residue was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 9:1) to afford N-{4-[2-cyano-1-(3-ethoxy-4-methoxy-phenyl)-vinyl]-phenyl}acetamide (0.4 g, 32%): mp 175-177° C.; 1H NMR (CDCl3) δ 7.51(d, J=8 Hz, 2H), 7.41 (s, 1H), 7.26 (d, J=9.0 Hz, 2H), 7.02-6.89 (m, 3H), 5.57 (s, 1H), 4.11-4.03 (q, J=7 Hz, 2H), 3.92 (s, 3H), 2.19 (s, 3H), 1.44 (t, J=7 Hz, 3H); 13C NMR (CDCl3) δ 168.38, 162.14, 150.93, 147.96, 139.91, 134.84, 129.58, 129.30, 123.08, 119.34, 118.53, 114.06, 111.01, 92.49, 64.53, 55.96, 24.65, 14.66; Anal Calcd for C20H20N2O3: C, 71.46; H, 5.99; N, 8.33. Found: C, 71.46, 6.01; N, 8.25. was extracted with EtOAc (3×50 mL) The combined organic extracts were washed with water (2×50 mL), brine (50 mL) dried (MgSO4) Solvent was removed the residue was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 9:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20 ml of triethylamine, 2.2 g (20 mmol) of indene, 5.22 , (20 mmol) of para-acetamino-iodo-benzene and 0.134 g (0.6 mmol) of Pd(OAc)2 were stirred under reflux for 10 h. After that all triethylamine was removed under reduced pressure. The residue was treated with the mixture 50 ml of dichloromethane and 50 ml of water. Organic layer was separated, washed twice with water, filtered and dried over Na2SO4. Dichloromethane was removed and the residue was recrystallized from 20 ml of EtOH. The yield of product was 13%. under reflux for 10 h After that all triethylamine was removed under reduced pressure The residue was treated with the mixture 50 ml of dichloromethane and 50 ml of water Organic layer was separated washed twice with water filtered dried over Na2SO4 Dichloromethane was removed the residue was recrystallized from 20 ml of EtOH

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20 ml of triethylamine, 2.2 g (20 mmol) of indene, 5.22 , (20 mmol) of para-acetamino-iodo-benzene and 0.134 g (0.6 mmol) of Pd(OAc)2 were stirred under reflux for 10 h. After that all triethylamine was removed under reduced pressure. The residue was treated with the mixture 50 ml of dichloromethane and 50 ml of water. Organic layer was separated, washed twice with water, filtered and dried over Na2SO4. Dichloromethane was removed and the residue was recrystallized from 20 ml of EtOH. The yield of product was 13%. under reflux for 10 h After that all triethylamine was removed under reduced pressure The residue was treated with the mixture 50 ml of dichloromethane and 50 ml of water Organic layer was separated washed twice with water filtered dried over Na2SO4 Dichloromethane was removed the residue was recrystallized from 20 ml of EtOH

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-Iodo-aniline (15 g, 69 mmol) in dry CH2Cl2 (100 ml) was added acetic anhydride(14.09 g, 138 mmol) at room temperature, the reaction mixture was then stirred for 2 hr. The gray color precipitate formed during the reaction was filtered, washed with ether and collected, the mother solution was concentrated to dryness and AcOEt was added, the resulting precipitate was filtered, washed with ether and combined with the previous solid as the desired product (15.95 g, 88.7%). The gray color precipitate formed during the reaction was filtered washed with ether collected the mother solution was concentrated to dryness and AcOEt was added the resulting precipitate was filtered washed with ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Iodoaniline (11.0 g, 50.4 mmol) was dissolved in 60 mL of ethyl acetate and the solution was added with 10 mL of acetic anhydride (10.8 g, 106 mmol) and 7.8 mL of pyridine (7.65 g, 99.4 mmol), and the mixture was stirred at room temperature for 2 hours with an equipment of a CaCl2 tube. A solvent was evaporated under reduced pressure to obtain 4-iodoacetanilide (yield: 13.0 g, percent yield: 99.0%). A solvent was evaporated under reduced pressure