chloromethyl N,N-diethylcarbamate

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: Stir a mixture of 3-(4-pyridinylamino)-1H-indole-2-carboxylic acid (2.0 g, 8.0 mmol), chloromethyl diethylcarbamate (1.7 g, 10.4 mmol) and K2CO3 in DMF (50 mL) at ambient temperature overnight. Add EtOAc (400 mL), to the reaction mixture, wash the organic layer with brine solution (400 mL) and concentrate to an oil. Purify by flash chromatography over silica gel (40 g) eluting with EtOAc and then 10% MeOH/EtOAc. Collect like fractions and concentrate under vacuum to yield an oil. Crystallize from heptane-ether to obtain 1.1 g (36%) of the title compound as a white powder: MS 383(M+H). Add EtOAc (400 mL), to the reaction mixture, wash the organic layer with brine solution (400 mL) concentrate to an oil Purify by flash chromatography over silica gel (40 g) eluting with EtOAc Collect like fractions concentrate under vacuum to yield an oil Crystallize from heptane-ether

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

Procedure: To a stirred solution of chloromethyl chloroformate (7.09 g, 5.5 mmol) in heptane (100 mL) at −20° C. add a solution of diethylamine (10.4 g, 14.7 mmol) in heptane (50 mL), dropwise. Maintain the internal temperature between −15° C. to −5° C. and after 1 h quench the reaction with water. Separate the layers and wash the organic phase with 10% aqueous HCl, water and NaHCO3 solution. Dry the organic layer (MgSO4), filter and concentrate under reduced pressure to obtain 8.3 g of the title compound. Maintain the internal temperature between −15° C. to −5° C. after 1 h quench the reaction with water Separate the layers wash the organic phase with 10% aqueous HCl, water and NaHCO3 solution Dry the organic layer (MgSO4) filter concentrate under reduced pressure

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