Sodium Carbonate → HCID 59177759, compound

HRID 423460Notes

Reaction equation

HRID 423460 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH:21]3[CH2:22][CH2:23][N:24]([C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]3)=[CH:17][CH:18]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 59177759HCID 59177759, compoundYield 18.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of [4-(methylthio)phenyl]boronic acid (16.8 mg, 0.1 mmol) and 1-methylethyl 4-{[(4-bromophenyl)oxy]methyl}-1-piperidinecarboxylate (36 mg, 0.10 mmol), Pd(PPh3)4 (5 mg, 0.004 mmol), 2M Na2CO3 (1 mL) and DME (1 mL) was heated at 80° C. overnight. The reaction was cooled to ambient temperature, transferred onto a 1 mL Varian Chem Elut column, eluted with EtOAc, and the filtrate concentrated. The crude product was purified by reverse-phase preparative HPLC using a MeOH:H2O gradient (20:80 to 100:0) with 0.1% formic acid as a modifier to afford the title compound (7.4 mg, 12%). LRMS (ESI), m/z 422 (M+Na).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. washeluted with EtOAc
  3. concentrationthe filtrate concentrated
  4. customThe crude product was purified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-e268411d4b0b402c8985058f2855557f
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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