4-(Phenylaminocarbonyl)benzeneboronic acid → 1-Methylethyl 4-[({4'-[(phenylamino)carbonyl]-4-biphenylyl}oxy)methyl]-1-piperidinecarboxylate

HRID 423468Notes

Reaction equation

HRID 423468 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][CH:37]([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]2)=[CH:22][CH:21]=1>>[C:1]1([NH:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH:28]4[CH2:29][CH2:30][N:31]([C:34]([O:36][CH:37]([CH3:39])[CH3:38])=[O:35])[CH2:32][CH2:33]4)=[CH:24][CH:25]=3)=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 110967474-(Phenylaminocarbonyl)benzeneboronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 591777961-Methylethyl 4-[({4'-[(phenylamino)carbonyl]-4-biphenylyl}oxy)methyl]-1-piperidinecarboxylateYield 16%

Procedure

The title compound (7.4 mg, 16%) was prepared from {4-[(phenylamino)carbonyl]phenyl}boronic acid (24.1 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 495 (M+Na).

Sources & evidence

ORD record
ord-1c6aca4fb60e49b0b352030724e4e725
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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