Sodium Carbonate → 1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-[({4'-[(1-methylethyl)thio]-4-biphenylyl}oxy)methyl]piperidine

HRID 423474Notes

Reaction equation

HRID 423474 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]3[O:33][N:32]=[C:31]([CH:34]([CH3:36])[CH3:35])[N:30]=3)[CH2:25][CH2:24]2)=[CH:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC>[CH3:36][CH:34]([C:31]1[N:30]=[C:29]([N:26]2[CH2:25][CH2:24][CH:23]([CH2:22][O:21][C:18]3[CH:17]=[CH:16][C:15]([C:8]4[CH:9]=[CH:10][C:5]([S:4][CH:2]([CH3:3])[CH3:1])=[CH:6][CH:7]=4)=[CH:20][CH:19]=3)[CH2:28][CH2:27]2)[O:33][N:32]=1)[CH3:35]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27734834-(Isopropylthio)benzeneboronic acidHCID 666732104-{[(4-Bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine

Product 1

HCID 666731951-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-[({4'-[(1-methylethyl)thio]-4-biphenylyl}oxy)methyl]piperidineYield 5.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-[({4′-[(1-methylethyl)thio]-4-biphenylyl}oxy)methyl]piperidine (20 mg, 5%) was prepared as a white solid from {4-[(1-methylethyl)thio]phenyl}boronic acid (167 mg, 0.85 mmol), 4-{[(4-bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine (322 mg, 0.85 mmol), Pd(PPh3)2Cl2 (50 mg, 0.07 mmol), 2M Na2CO3 (5 mL) and DME (5 mL) in a manner similar to Example 21, Step 3. 1H NMR (400 MHz, CDCl3): δ 7.57-7.39 (m, 6H), 6.94 (d, 2H, J=8.9 Hz), 4.28-4.18 (m, 2H), 3.87 (d, 2H, J=6.4 Hz), 3.46-3.30 (m, 1H), 3.20-3.08 (m, 2H), 2.98-2.85 (m, 1H), 2.16-2.03 (m, 1H), 2.03-1.93 (m, 2H), 1.55-1.39 (m, 2H), 1.36-1.24 (m, 12H); LRMS (ESI), m/z 452 (M+H).

Sources & evidence

ORD record
ord-e79ecfd7913d4091a06e8fa7f0f51c08
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

Loading…