4-(Trifluoromethoxy)phenylboronic acid → (3,5-Dimethyl-4'-trifluoromethoxy-biphenyl-4-yl)-(4-hydroxy-[1,4']bipiperidinyl-1'-yl)-methanone

HRID 1692414Notes

Reaction equation

HRID 1692414 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[O:10])=[C:4]([CH3:24])[CH:3]=1.[F:25][C:26]([F:38])([F:37])[O:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1>>[CH3:24][C:4]1[CH:3]=[C:2]([C:31]2[CH:30]=[CH:29][C:28]([O:27][C:26]([F:25])([F:37])[F:38])=[CH:33][CH:32]=2)[CH:7]=[C:6]([CH3:8])[C:5]=1[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]2)[CH2:13][CH2:12]1)=[O:10]

Participants

3

Reactant 2

HCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 66901547(4-Bromo-2,6-dimethyl-phenyl)-(4-hydroxy-[1,4']bipiperidinyl-1'-yl)-methanone

Product 1

HCID 57580521(3,5-Dimethyl-4'-trifluoromethoxy-biphenyl-4-yl)-(4-hydroxy-[1,4']bipiperidinyl-1'-yl)-methanone

Procedure

In analogy to the procedure described for example 1, (4-bromo-2,6-dimethyl-phenyl)-(4-hydroxy-[1,4′]bipiperidinyl-1′-yl)-methanone (example 22) was reacted with 4-trifluoromethoxy-phenyl boronic acid to give the title compound as light yellow solid. MS: 477.2 (MH+).

Sources & evidence

ORD record
ord-09ddef9085794a1dbd1f84ca7fd7e7d6
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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