3-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride) → (3,5-Dimethyl-3'-trifluoromethoxy-biphenyl-4-yl)-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone

HRID 1692403Notes

Reaction equation

HRID 1692403 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.[F:25][C:26]([F:38])([F:37])[O:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1>>[CH3:24][C:4]1[CH:3]=[C:2]([C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([O:27][C:26]([F:25])([F:37])[F:38])[CH:29]=2)[CH:7]=[C:6]([CH3:8])[C:5]=1[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:21][CH2:20][CH2:19][C@H:18]2[CH2:22][OH:23])[CH2:13][CH2:12]1)=[O:10]

Participants

3

Reactant 2

HCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 44473778(4-Bromo-2,6-dimethyl-phenyl)-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone2×

Product 1

HCID 57580546(3,5-Dimethyl-3'-trifluoromethoxy-biphenyl-4-yl)-[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-trifluoromethoxy-phenyl boronic acid to give the title compound as off-white solid. MS: 477.2 (MH+).

Sources & evidence

ORD record
ord-b7efbe7b9d5a4ebf8804fd2ee76effda
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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