4-(Trifluoromethyl)phenylboronic acid → 1-Methylethyl 4-({[4'-(trifluoromethyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylate

HRID 423461Notes

Reaction equation

HRID 423461 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)=[CH:17][CH:16]=1>>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH:23]3[CH2:24][CH2:25][N:26]([C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]3)=[CH:19][CH:20]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 591777631-Methylethyl 4-({[4'-(trifluoromethyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylateYield 5.2%

Procedure

The title compound (2.2 mg, 5%) was prepared from [4-(trifluoromethyl)phenyl]boronic acid (19 mg, 0.1 mmol) and 1-methylethyl 4-{[(4-bromophenyl)oxy]methyl}-1-piperidinecarboxylate (Example 9, Step 2, 36 mg, 0.10 mmol) in a manner similar to Example 9, Step 3. LRMS (ESI), m/z 444 (M+Na).

Sources & evidence

ORD record
ord-05990a600283407c9d3ce4e65c2c72b8
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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