4-(Isopropylthio)benzeneboronic acid → 1-Methylethyl 4-[({4'-[(1-methylethyl)thio]-4-biphenylyl}oxy)methyl]-1-piperidinecarboxylate

HRID 423463Notes

Reaction equation

HRID 423463 reaction equation
[CH3:1][CH:2]([S:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)[CH3:3].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>>[CH3:1][CH:2]([S:4][C:5]1[CH:10]=[CH:9][C:8]([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:7][CH:6]=1)[CH3:3]

Participants

3

Reactant 2

HCID 27734834-(Isopropylthio)benzeneboronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 591777541-Methylethyl 4-[({4'-[(1-methylethyl)thio]-4-biphenylyl}oxy)methyl]-1-piperidinecarboxylateYield 17%

Procedure

The title compound (7.1 mg, 17%) was prepared from {4-[(1-methylethyl)thio]phenyl}boronic acid (19.6 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 450 (M+Na).

Sources & evidence

ORD record
ord-726d6d6b441d4faa8530642549ef342f
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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