Ammonia → tert-butyl (S)-2-({4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]phenylamino}methyl)pyrrolidine-1-carboxylate

https://huagongshe.com/ja/reaction/734865

関与物質

役割	名称	HCID	仕込み量
反応物	Ammonia	HCID 222	—
反応物	Diethylsalicylamide	HCID 88006	—
反応物	tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylate	HCID 1512533	—
反応物	Potassium phosphate, tribasic, monohydrate	HCID 22031701	—
反応物	5-(4-Chlorophenyl)-2-(4-iodophenylethynyl)pyridine	HCID 69059929	—
触媒	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
溶媒	Dimethylformamide	HCID 6228	—
溶媒	Ethyl Acetate	HCID 8857	—
生成物	tert-butyl (S)-2-({4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]phenylamino}methyl)pyrrolidine-1-carboxylate	HCID 57845306	—

反応条件

温度	100 °C

反応手順

4.90 g (20.00 mmol) of potassium phosphate monohydrate were added under argon to a mixture of 4.16 g (10.00 mmol) of 5-(4-chlorophenyl)-2-(4-iodophenylethynyl)pyridine, 3.10 g (15.00 mmol) of tert-butyl (S)-2-aminomethylpyrrolidine-1-carboxylate, 194 mg (1.00 mmol) of CuI, 0.77 g (4.00 mmol) of N,N-diethylsalicylamide in 10 mL of DMF and the mixture was stirred for 16 hours at 100° C. The reaction mixture was combined with 100 mL of 5% aqueous ammonia, stirred, and the precipitate was filtered off. The precipitate was purified by MPLC (Hyperprep HS C18, 8 μm, gradient 0.15% formic acid in water/acetonitrile 10/90→90/10 v/v). 2 fractions were isolated. Fraction 1: yield: 0.48 g (10% of theoretical); C29H30ClN3O2 (M=488.020) molpeak (M+H)+: 488/490 (Cl); found: molpeak (M+H)+: 488/490 (Cl); Rf value: 0.60 (silica gel, PE/EtOAc 1:1).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07592358B2
出典データセット	uspto-grants-2009_09
ORD ID	ord-dc3cf34d9e2045688d4114cd2f6b3540
出典メモ	uspto-grants-2009_09