5-Cyanopyridine-3-boronic acid → 5-((2RS,4R)-3'-amino-6',6'-difluoro-2-phenyl-6',7'-dihydro-2'H-spiro[chroman-4,5'-[1,4]oxazepine]-6-yl)nicotinonitrile

HRID 1525199Notes

Reaction equation

HRID 1525199 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@@:11]3([C:17]([F:19])([F:18])[CH2:16][O:15][CH2:14][C:13]([NH2:20])=[N:12]3)[CH2:10][CH:9]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:8][C:5]2=[CH:6][CH:7]=1.[C:27]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[N:33][CH:34]=1)#[N:28]>>[NH2:20][C:13]1[CH2:14][O:15][CH2:16][C:17]([F:19])([F:18])[C@@:11]2([C:4]3[C:5](=[CH:6][CH:7]=[C:2]([C:31]4[CH:32]=[N:33][CH:34]=[C:29]([CH:30]=4)[C:27]#[N:28])[CH:3]=3)[O:8][CH:9]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:10]2)[N:12]=1

Participants

3

Reactant 2

HCID 450795765-Cyanopyridine-3-boronic acidHCID 71059735(2RS,4R)-6-bromo-6',6'-difluoro-2-phenyl-6',7'-dihydro-2'H-spiro[chroman-4,5'-[1,4]oxazepin]-3'-amine

Product 1

HCID 710600105-((2RS,4R)-3'-amino-6',6'-difluoro-2-phenyl-6',7'-dihydro-2'H-spiro[chroman-4,5'-[1,4]oxazepine]-6-yl)nicotinonitrileYield 15%

Procedure

The cross coupling reaction of (2RS,4R)-6-bromo-6′,6′-difluoro-2-phenyl-6′,7′-dihydro-2′H-spiro[chroman-4,5′-[1,4]oxazepin]-3′-amine (intermediate C3.4) with 5-cyanopyridin-3-ylboronic acid yielded the title compound (15% yield) as a colorless solid. MS (ISP): m/z=447.4 [M+H]+.

Sources & evidence

ORD record
ord-c123363c690d4885875559fc02d107c2
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

Loading…