Sodium Hydroxide → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-[4-(methoxy)phenyl]-1-benzofuran-2-carboxamide hydrochloride

참여 물질

역할	이름	HCID	투입량
반응물	Sodium Hydroxide	HCID 14798	—
반응물	(4-Methoxyphenyl)boronic acid	HCID 201262	—
반응물	N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-bromo-1-benzofuran-2-carboxamide hydrochloride	HCID 67314004	—
촉매	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
용매	Dimethylformamide	HCID 6228	—
생성물	N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-[4-(methoxy)phenyl]-1-benzofuran-2-carboxamide hydrochloride	HCID 67313861	—

반응 조건

온도	90 °C

반응 단계

130 mg (0.86 mmol) of 4-(methoxy)phenylboronic acid and 2.15 ml of 1N sodium hydroxide solution are added to a mixture of 250 mg (0.72 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-5-bromo-1-benzofuran-2-carboxamide (Example 3A) and 52 mg (0.07 mmol) of PdCl2(dppf) in 3 ml of DMF. The reaction mixture is heated at 90° C. overnight. The solvent is removed under reduced pressure, and the crude product is taken up in methanol and filtered through kieselguhr. Purification takes place by preparative HPLC. The product fractions are mixed with an excess of 1N hydrochloric acid. The solvent is removed under reduced pressure. Drying under high vacuum results in 127 mg (39% of theory) of the title compound.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US07977485B2
출처 데이터셋	uspto-grants-2011_07
ORD ID	ord-f801db090ea2454a805d38ad2799de10
출처 메모	uspto-grants-2011_07