(4-(Methylsulfinyl)phenyl)boronic acid → (+/-)-1-Methylethyl 4-({[4'-(methylsulfinyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylate

HRID 423464Notes

Reaction equation

HRID 423464 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)=[O:3].Br[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)=[CH:16][CH:15]=1>>[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH:22]3[CH2:23][CH2:24][N:25]([C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29])[CH2:26][CH2:27]3)=[CH:18][CH:19]=2)=[CH:6][CH:5]=1)=[O:3]

Participants

3

Reactant 2

HCID 2773531(4-(Methylsulfinyl)phenyl)boronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 59177838(+/-)-1-Methylethyl 4-({[4'-(methylsulfinyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylateYield 16%

Procedure

The title compound (6.6 mg, 16%) was prepared from (±)-[4-(methylsulfinyl)phenyl]boronic acid (18.4 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 416 (M+H).

Sources & evidence

ORD record
ord-c36b82f422634eaeb7a90e23b7b4def4
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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