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

HRID 1525175Notes

Reaction equation

HRID 1525175 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@@:11]3([C:16]([F:18])([F:17])[CH2:15][O:14][C:13]([NH2:19])=[N:12]3)[CH2:10][CH:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:8][C:5]2=[CH:6][CH:7]=1.[N:26]1[CH:31]=[C:30](B(O)O)[CH:29]=[N:28][CH:27]=1>>[F:17][C:16]1([F:18])[CH2:15][O:14][C:13]([NH2:19])=[N:12][C@@:11]21[C:4]1[C:5](=[CH:6][CH:7]=[C:2]([C:30]3[CH:31]=[N:26][CH:27]=[N:28][CH:29]=3)[CH:3]=1)[O:8][CH:9]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:10]2

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 71059462(2RS,4R)-6-bromo-5',5'-difluoro-2-phenyl-5',6'-dihydrospiro[chroman-4,4'-[1,3]oxazin]-2'-amine

Product 1

HCID 71059660(2RS,4R)-5',5'-difluoro-2-phenyl-6-(pyrimidin-5-yl)-5',6'-dihydrospiro[chroman-4,4'-[1,3]oxazin]-2'-amineYield 22%

Procedure

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 pyrimidin-5-ylboronic acid yielded the title compound (22% yield) as a white solid. MS (ISP): m/z=409.3 [M+H]+.

Sources & evidence

ORD record
ord-7c36170389334b22806c681ede78dbcc
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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