4-Benzoylbenzeneboronic acid → 1-Methylethyl 4-({[4'-(phenylcarbonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylate

HRID 423469Notes

Reaction equation

HRID 423469 reaction equation
[C:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]2)=[CH:21][CH:20]=1>>[C:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH:27]4[CH2:28][CH2:29][N:30]([C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])[CH2:31][CH2:32]4)=[CH:23][CH:24]=3)=[CH:11][CH:10]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 41972354-Benzoylbenzeneboronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 591778351-Methylethyl 4-({[4'-(phenylcarbonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylateYield 7%

Procedure

The title compound (3.0 mg, 7%) was prepared from [4-(phenylcarbonyl)phenyl]boronic acid (22.6 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 480 (M+Na).

Sources & evidence

ORD record
ord-4d0657e550c64b0fa053ea06e42294f1
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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