3-iodobenzoyl chloride

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: A stirred suspension of 3-iodobenzoic acid (8.84 g) in thionyl chloride (44 mL) is heated at reflux for 30 minutes. The dark brown solution is evaporated to give 3-iodobenzoyl chloride (9.8 g) as a brown oil. is heated at reflux for 30 minutes The dark brown solution is evaporated

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

Procedure: A stirred solution of N-methoxymethylamine (3.47 g) and triethylamine (10.4 mL) in dichloromethane (100 mL) at 5° C. is treated dropwise with 3-iodobenzoyl chloride (9.8 g). The reaction mixture is stirred at room temperature for 2 hours, washed twice with water (70 mL), dried over magnesium sulphate, and evaporated to give N-methoxy-N-methyl-3-iodobenzamide (9.8 g) as a brown oil. washed twice with water (70 mL) dried over magnesium sulphate evaporated

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

Procedure: To a cooled (0° C.) solution of 3-iodobenzoyl chloride (2.66 g; 10.0 mmol) in DCM (10 mL) was slowly added a 2 M solution of methylamine in THF (10 mL, 2.0 eq.). Upon completion of the addition, the ice bath was removed and the mixture was stirred overnight. All volatiles were removed in vacuo and the residue was treated with aq. NaHCO3 (25 mL) and subsequently extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica gel to give the desired 3-iodo-N-methylbenzamide (0.67 g, 26% yield). Upon completion of the addition the ice bath was removed All volatiles were removed in vacuo the residue was treated with aq. NaHCO3 (25 mL) subsequently extracted with ethyl acetate (3×15 mL) The combined organic layers were dried over MgSO4 evaporated The crude product was purified by column chromatography on silica gel

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

Procedure: The 3-(3-iodo-phenyl)-3-oxo-propionic acid was prepared from 3-iodobenzoyl chloride (21.0 g, 78.8 mmol) and bis(trimethylsilyl)malonate (21.0 mL, 82.8 mmol) with Et3N (23 mL, 165.5 mmol) and LiBr (7.54 g, 86.7 mmol) in CH3CN at 0° C. according to general procedure H (method c1). The crude material (21.9 g) was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure J (method a). Obtained as a yellow solid (9.6 g).

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

Procedure: 1.5 g of C,C-dipyridin-2-yl-methylamine are suspended in 50 ml of methylene chloride and 1.15 ml of triethylamine and treated dropwise at 0° with a solution of 3-iodo-benzoyl chloride. After 1 hr. at 0° the reddish suspension is concentrated, the residue is poured into water and extracted three times with methylene chloride. Chromatography on silica gel with methylene chloride/methanol 9:1 yields 1.31 g of brownish N-(di-pyridin-2-yl-methyl)-3-iodo-benzamide. Yield: 39%. Mass spectrum: peaks inter alia at m/e: 415 (M+, 8%), 320 (44%), 231 (36%), 184 (100%). at 0° the reddish suspension is concentrated the residue is poured into water extracted three times with methylene chloride

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

Procedure: N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-iodobenzamide was prepared according to method C with triethylamine (2.23 mL; 15.90 mmol), 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (1.5 g; 6.36 mmol) and 3-iodobenzoyl chloride (1.82 g; 6.68 mmol) in dichloromethane (75 mL). The mixture was stirred for 20 minutes at room temperature and was evaporated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in dichloromethane) to provide 2.56 g (95%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-iodobenzamide as a white solid. N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-iodobenzamide was prepared was evaporated under reduced pressure The crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in dichloromethane)

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

Procedure: The 3-(3-iodo-phenyl)-3-oxo-propionic acid was prepared from 3-iodobenzoyl chloride (21.0 g, 78.8 mmol) and bis(trimethylsilyl)malonate (21.0 mL, 82.8 mmol) with Et3N (23 mL, 165.5 mmol) and LiBr (7.54 g, 86.7 mmol) in CH3CN at 0° C. according to general procedure H (method c1). The crude material (21.9 g) was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure J (method a). Obtained as a yellow solid (9.6 g).

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

Procedure: The 3-(3-iodo-phenyl)-3-oxo-propionic acid was prepared from 3-iodobenzoyl chloride (21.0 g, 78.8 mmol) and bis(trimethylsilyl)malonate (21.0 mL, 82.8 mmol) with Et3N (23 mL, 165.5 mmol) and LiBr (7.54 g, 86.7 mmol) in CH3CN at 0° C. according to general procedure H (method c1). The crude material (21.9 g) was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure J (method a). Obtained as a yellow solid (9.6 g).