(4-Bromo-2,6-dimethyl-phenyl)-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone → [2,6-Dimethyl-4-(5-trifluoromethyl-pyridin-3-yl)-phenyl]-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone

HRID 1692406Notes

Reaction equation

HRID 1692406 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[CH2:21][CH2:20][CH2:19][C@H:18]3[CH2:22][OH:23])[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[CH2:21][CH2:20][CH2:19][C@H:18]2[CH2:22][OH:23])[CH2:13][CH2:12]1)=[O:10]

Participants

3

Reactant 2

HCID 44473778(4-Bromo-2,6-dimethyl-phenyl)-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone2×HCID 533979043-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)pyridine2×

Product 1

HCID 25190016[2,6-Dimethyl-4-(5-trifluoromethyl-pyridin-3-yl)-phenyl]-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone

Procedure

In analogy to the procedure described for example 1, (4-bromo-2,6-dimethyl-phenyl)-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone (intermediate 4) 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 solid. MS: 462.4 (MH+).

Sources & evidence

ORD record
ord-0a6e40e751814c35942ff7a7ffc21f29
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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