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

HRID 1525174Notes

Reaction equation

HRID 1525174 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.[C:26]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[N:32][CH:33]=1)#[N:27]>>[NH2:19][C:13]1[O:14][CH2:15][C:16]([F:18])([F:17])[C@@:11]2([C:4]3[C:5](=[CH:6][CH:7]=[C:2]([C:30]4[CH:31]=[N:32][CH:33]=[C:28]([CH:29]=4)[C:26]#[N:27])[CH:3]=3)[O:8][CH:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:10]2)[N:12]=1

Participants

3

Reactant 2

HCID 450795765-Cyanopyridine-3-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 710597275-((2RS,4R)-2'-amino-5',5'-difluoro-2-phenyl-5',6'-dihydrospiro[chroman-4,4'-[1,3]oxazine]-6-yl)nicotinonitrileYield 16%

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 5-cyanopyridin-3-ylboronic acid yielded the title compound (16% yield) as a white solid. MS (ISP): m/z=433.3 [M+H]+.

Sources & evidence

ORD record
ord-dfbc32ee094247d9b0cd54dcb023b2d8
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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