3-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)pyridine → [2,6-Dimethyl-4-(5-trifluoromethyl-pyridin-3-yl)-phenyl]-(4-hydroxy-[1,4']bipiperidinyl-1'-yl)-methanone

HRID 1692415Notes

Reaction equation

HRID 1692415 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.CC1(C)C(C)(C)OB([C:33]2[CH:34]=[N:35][CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=2)O1>>[CH3:8][C:6]1[CH:7]=[C:2]([C:33]2[CH:34]=[N:35][CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=2)[CH:3]=[C:4]([CH3:24])[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 533979043-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)pyridine2×HCID 66901547(4-Bromo-2,6-dimethyl-phenyl)-(4-hydroxy-[1,4']bipiperidinyl-1'-yl)-methanone

Product 1

HCID 57580556[2,6-Dimethyl-4-(5-trifluoromethyl-pyridin-3-yl)-phenyl]-(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 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-pyridine (intermediate 6) to give the title compound as light yellow oil. MS: 462.2 (MH+).

Sources & evidence

ORD record
ord-b0994506b1ac4761a8bcb1973d298f03
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

Loading…