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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1525173Generated: November 5, 2026

5-Chloropyridine-3-boronic acid → (2RS,4R)-6-(5-chloropyridin-3-yl)-5',5'-difluoro-2-phenyl-5',6'-dihydrospiro[chroman-4,4'-[1,3]oxazin]-2'-amine

https://huagongshe.com/reaction/1525173

Reaction equation

Participants

RoleNameHCIDCharge
Reactant5-Chloropyridine-3-boronic acidHCID 20111877—
Reactant(2RS,4R)-6-bromo-5',5'-difluoro-2-phenyl-5',6'-dihydrospiro[chroman-4,4'-[1,3]oxazin]-2'-amineHCID 71059462—
Product(2RS,4R)-6-(5-chloropyridin-3-yl)-5',5'-difluoro-2-phenyl-5',6'-dihydrospiro[chroman-4,4'-[1,3]oxazin]-2'-amineHCID 7105966916%

Reaction Steps

In a manner analogous to that described in Example 19, the cross coupling reaction of (2RS,4R)-6-bromo-5′,5′-difluoro-2-phenyl-5′,6′-dihydrospiro[chroman-4,4′-[1,3]oxazin]-2′-amine (intermediate B6.3) with 5-chloropyridin-3-ylboronic acid yielded the title compound (16% yield) as a grey solid. MS (ISP): m/z=442.3 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09079919B2
Source datasetuspto-grants-2015_07
ORD IDord-6ef8596f0ed2468c99d41db9ebb2ed32
Source noteuspto-grants-2015_07