phenyl formate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The 3-(2'-methyl-2'-aminobutyl)-indole obtained as reduction product in accordance with Example 1 or 3 was reacted with phenyl formate to yield 3-(2'-methyl-2'-formylaminobutyl)-indole; melting point 121.5°-124.5°C. (from ether). Reduction thereof with LiAlH4 yielded 3-(2'-methyl-2'-methylaminobutyl)-indole having a melting point of 100°-103°C. (from cyclohexane).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The 3-(2'-methyl-2'-aminobutyl)-indole obtained as reduction product in accordance with Example 1 or 3 was reacted with phenyl formate to yield 3-(2'-methyl-2'-formylaminobutyl)-indole; melting point 121.5°-124.5°C. (from ether). Reduction thereof with LiAlH4 yielded 3-(2'-methyl-2'-methylaminobutyl)-indole having a melting point of 100°-103°C. (from cyclohexane).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Formic acid phenyl ester 7 may be synthesized from the corresponding benzaldehyde via traditional oxidation methods known in the art. For example, Baeyer-Villiger oxidation using m-CPBA to form 7, followed by deformylation using a suitable base and exposure to bromide 8 affords stilbene analog 9. to form 7

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Formic acid phenyl ester 7 may be synthesized from the corresponding benzaldehyde via traditional oxidation methods known in the art. For example, Baeyer-Villiger oxidation using m-CPBA to form 7, followed by deformylation using a suitable base and exposure to bromide 8 affords stilbene analog 9. to form 7

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound is prepared in 86% yield (287 mg, brown oil) from 4-chloro-2-(1-(6-((4-fluorobenzyl)oxy)-5-methylpyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one (276 mg, 0.67 mmol, Intermediate-125, single enantiomer) and phenyl formate (164 mg, 1.34 mmol) in a similar manner to Intermediate-91.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound is prepared in 86% yield (287 mg, brown oil) from 4-chloro-2-(1-(6-((4-fluorobenzyl)oxy)-5-methylpyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one (276 mg, 0.67 mmol, Intermediate-125, single enantiomer) and phenyl formate (164 mg, 1.34 mmol) in a similar manner to Intermediate-91.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound is prepared in 45% yield (275 mg, white solid) from 4-chloro-2-(1-(6-(cyclopropylmethoxy)-5-methylpyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one (492 mg, 1.37 mmol, Intermediate-124, single enantiomer) and phenyl formate (336 mg, 1.37 mmol) in a similar manner to Intermediate-91.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound is prepared in 90% yield (280 mg, brown oil) from tert-butyl 4-((4-chloro-1-oxo-1H-pyrrolo[3,4-c]pyridin-2(3H)-yl)methyl)-2-methylbenzoate (250 mg, 0.67 mmol, Step-1) and phenyl formate (160 mg, 1.3 mmol) in a similar manner to Intermediate-91.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound is prepared in 79% yield (140 mg, pale brown solid) from 4-chloro-2-(1-(5-chloro-6-(3,3,3-trifluoropropoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one (150 mg, 0.36 mmol, Intermediate-78, single enantiomer) and phenyl formate (87 mg, 0.71 mmol) in a similar manner to Intermediate-91.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound is prepared in 74% yield (230 mg, pale brown solid) from 4-chloro-2-(1-(5-chloro-6-(2,2-difluoropropoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one (250 mg, 0.62 mmol, Intermediate-80, single enantiomer) and phenyl formate (150 mg, 1.2 mmol) in a similar manner to Intermediate-91.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound is prepared in 70% yield (130 mg, brown oil) from 4-chloro-2-(1-(5-chloro-6-(2,2,3,3-tetrafluoropropoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one (150 mg, 0.34 mmol, Intermediate-77, single enantiomer) and phenyl formate (84 mg, 0.69 mmol) in a similar manner to Intermediate-91.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound is prepared in 70% yield (130 mg, brown oil) from 4-chloro-2-(1-(5-chloro-6-(2,2,3,3-tetrafluoropropoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one (150 mg, 0.34 mmol, Intermediate-77, single enantiomer) and phenyl formate (84 mg, 0.69 mmol) in a similar manner to Intermediate-91.