(Pyrimidin-5-yl)boronic acid → (2RS,4R)-6',6'-difluoro-2-phenyl-6-(pyrimidin-5-yl)-6',7'-dihydro-2'H-spiro[chroman-4,5'-[1,4]oxazepin]-3'-amine

HRID 1525198Notes

Reaction equation

HRID 1525198 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.[N:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[N:29][CH:28]=1>>[F:18][C:17]1([F:19])[CH2:16][O:15][CH2:14][C:13]([NH2:20])=[N:12][C@@:11]21[C:4]1[C:5](=[CH:6][CH:7]=[C:2]([C:31]3[CH:32]=[N:27][CH:28]=[N:29][CH:30]=3)[CH:3]=1)[O:8][CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:10]2

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)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 71059517(2RS,4R)-6',6'-difluoro-2-phenyl-6-(pyrimidin-5-yl)-6',7'-dihydro-2'H-spiro[chroman-4,5'-[1,4]oxazepin]-3'-amineYield 12%

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 pyrimidin-5-ylboronic acid yielded the title compound (12% yield). MS (ISP): m/z=423.0 [M+H]+.

Sources & evidence

ORD record
ord-69266a21c9c7402ea347086820049774
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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