3,5-Dichlorophenylboronic acid → (2RS,4R)-6-(3,5-dichlorophenyl)-5',5'-difluoro-2-phenyl-5',6'-dihydrospiro[chroman-4,4'-[1,3]oxazin]-2'-amine

HRID 1525176Notes

Reaction equation

HRID 1525176 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.[Cl:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[C:31]([Cl:33])[CH:32]=1>>[Cl:26][C:27]1[CH:28]=[C:29]([C:2]2[CH:3]=[C:4]3[C@@:11]4([C:16]([F:18])([F:17])[CH2:15][O:14][C:13]([NH2:19])=[N:12]4)[CH2:10][CH:9]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[O:8][C:5]3=[CH:6][CH:7]=2)[CH:30]=[C:31]([Cl:33])[CH:32]=1

Participants

3

Reactant 2

HCID 27343313,5-Dichlorophenylboronic 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 71059344(2RS,4R)-6-(3,5-dichlorophenyl)-5',5'-difluoro-2-phenyl-5',6'-dihydrospiro[chroman-4,4'-[1,3]oxazin]-2'-amineYield 17%

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 3,5-dichlorophenylboronic acid yielded the title compound (17% yield) as a white solid. MS (ISP): m/z=475.0 [M+H]+.

Sources & evidence

ORD record
ord-dbea0317440141b49f0b0ca0cb4fa4a7
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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