HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-Cyanopyridine-3-boronic acid → 5-((2RS,4R)-2'-amino-5',5'-difluoro-2-phenyl-5',6'-dihydrospiro[chroman-4,4'-[1,3]oxazine]-6-yl)nicotinonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-Cyanopyridine-3-boronic acid | HCID 45079576 | — |
| Reactant | (2RS,4R)-6-bromo-5',5'-difluoro-2-phenyl-5',6'-dihydrospiro[chroman-4,4'-[1,3]oxazin]-2'-amine | HCID 71059462 | — |
| Product | 5-((2RS,4R)-2'-amino-5',5'-difluoro-2-phenyl-5',6'-dihydrospiro[chroman-4,4'-[1,3]oxazine]-6-yl)nicotinonitrile | HCID 71059727 | 16% |
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-cyanopyridin-3-ylboronic acid yielded the title compound (16% yield) as a white solid. MS (ISP): m/z=433.3 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09079919B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-dfbc32ee094247d9b0cd54dcb023b2d8 |
| Source note | uspto-grants-2015_07 |