2,2,3,3,4,4,4-heptafluorobutanoyl 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:; See reaction.notes.procedure_details.

Procedure: 5-(Trifluoromethyl)-3-nitro-2-aminopyridine is reacted with perfluorobutyryl chloride to yield 5-(trifluoromethyl)-3-nitro-2-(2,2,3,3,4,4,4-heptafluorobutyramido)pyridine, which when hydrogenated yields 6-(trifluoromethyl)-1-hydroxy-2-(perfluoro-n-propyl)-1H-imidazo(4,5-b)pyridine.

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

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

Procedure: 5-(Trifluoromethyl)-3-nitro-2-aminopyridine is reacted with perfluorobutyryl chloride to yield 5-(trifluoromethyl)-3-nitro-2-(2,2,3,3,4,4,4-heptafluorobutyramido)pyridine, which when hydrogenated yields 6-(trifluoromethyl)-1-hydroxy-2-(perfluoro-n-propyl)-1H-imidazo(4,5-b)pyridine.

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

Procedure: 5-Methyl-7-phenyl-2,3-dihydro-1H-pyrrolizine (Example 30 c, 1.0 g, 0.005 mol), dissolved in dichloroethane (20 ml) is treated with heptafluorobutyryl chloride (0.83 ml, 1.3 g, 0.0055 mol) at RT and finally tin tetrachloride (0.7 ml, 1,56 g, 0.006 mol) in dichloroethane (5 ml) is added dropwise. The mixture warms to 35° C. and is stirred at RT for 16 h. The GC-MS analysis shows a 60% reaction. The reaction mixture is rendered alkaline with NaOH (25%, 25 ml) in an ice bath and, after addition of CH2Cl2 (25 ml), the organic phase is separated in a separating funnel. The alkali phase is extracted a further two times with dichloromethane (2×20 ml). These CH2Cl2 extracts are combined, dried over Na2SO4 sicc. and evaporated to dryness in vacuo. warms to 35° C. a 60% reaction the organic phase is separated in a separating funnel The alkali phase is extracted a further two times with dichloromethane (2×20 ml) dried over Na2SO4 sicc and evaporated to dryness in vacuo

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: With stirring and at −10° C., 21.7 g (93.2 mmol) of heptafluorobutyryl chloride—dissolved in 50 ml of dichloromethane—were added to a mixture of 8.11 g (102 mmol) of pyridine and 9.33 g (93.2 mmol) of butyl vinyl ether in 200 ml of dichloromethane. After the addition, stirring was continued at room temperature for another 15 h. 300 ml of water were then added to the mixture, and the organic phase was separated off, dried and concentrated. After the addition stirring the organic phase was separated off dried concentrated

Conditions: temp:6.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.60 cm3 of heptafluorobutyryl chloride is added to 1 g of 6-chloro-1H-indazole-3-amine in 10 cm3 of pyridine, after cooling the medium to about 6° C., the mixture is then allowed to return to room temperature over 19 hours and is evaporated to dryness under reduced pressure (2 kPa; 45° C.). The residue is taken up in 40 cm3 of ethyl acetate and 20 cm3 of water; the precipitate formed is filtered off on a sinter funnel and then rinsed with 2×10 cm3 of methylene chloride and purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 3.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.) to give 0.77 g of N-[6-chloro-1H-indazol-3-yl]-2,2,3,3,4,4,4-heptafluorobutanamide in cottony form. is evaporated to dryness under reduced pressure (2 kPa; 45° C.) the precipitate formed is filtered off on a sinter funnel rinsed with 2×10 cm3 of methylene chloride purified by chromatography under an argon pressure of 50 kPa on a column of silica gel (particle size 40-60 μm; diameter 3.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume) The fractions containing the expected product evaporated under reduced pressure (2 kPa; 50° C.)

Conditions: temp:6.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.60 cm3 of heptafluorobutyryl chloride is added to 1 g of 6-chloro-1H-indazole-3-amine in 10 cm3 of pyridine, after cooling the medium to about 6° C., the mixture is then allowed to return to room temperature over 19 hours and is evaporated to dryness under reduced pressure (2 kPa; 45° C.). The residue is taken up in 40 cm3 of ethyl acetate and 20 cm3 of water; the precipitate formed is filtered off on a sinter funnel and then rinsed with 2×10 cm3 of methylene chloride and purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 3.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.) to give 0.77 g of N-[6-chloro-1H-indazol-3-yl]-2,2,3,3,4,4,4-heptafluorobutanamide in cottony form. is evaporated to dryness under reduced pressure (2 kPa; 45° C.) the precipitate formed is filtered off on a sinter funnel rinsed with 2×10 cm3 of methylene chloride purified by chromatography under an argon pressure of 50 kPa on a column of silica gel (particle size 40-60 μm; diameter 3.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume) The fractions containing the expected product evaporated under reduced pressure (2 kPa; 50° C.)

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

Procedure: 5-(Trifluoromethyl)-3-nitro-2-aminopyridine is reacted with perfluorobutyryl chloride to yield 5-(trifluoromethyl)-3-nitro-2-(2,2,3,3,4,4,4-heptafluorobutyramido)pyridine, which when hydrogenated yields 6-(trifluoromethyl)-1-hydroxy-2-(perfluoro-n-propyl)-1H-imidazo(4,5-b)pyridine.

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

Procedure: 5-(Trifluoromethyl)-3-nitro-2-aminopyridine is reacted with perfluorobutyryl chloride to yield 5-(trifluoromethyl)-3-nitro-2-(2,2,3,3,4,4,4-heptafluorobutyramido)pyridine, which when hydrogenated yields 6-(trifluoromethyl)-1-hydroxy-2-(perfluoro-n-propyl)-1H-imidazo(4,5-b)pyridine.