Sodium Carbonate → HCID 24994334, compound

HRID 423514Notes

Reaction equation

HRID 423514 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:15]1[N: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.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>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:15]2[N:20]=[CH:19][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:17][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 866387374-(6-Bromopyridin-3-yloxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 24994334HCID 24994334, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Alternative preparation: [4-(Methylsulfonyl)phenyl]boronic acid (0.17 g, 0.84 mmol) and 1-methylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 81, Step 1, 0.25 g, 0.70 mmol) were mixed with DME (4 mL) and 2M Na2CO3 (4 mL). The mixture was degassed with N2, then PdCl2(PPh3)2 (50 mg, 0.07 mmol) was added. The reaction mixture was degassed again with N2 and heated at 80° C. for 6 h, then cooled to ambient temperature, and diluted with EtOAc. The mixture was washed with water and brine and the organic layer was dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a brown solid. The crude product was purified by chromatography on a silica gel column eluted with 25% EtOAc/CH2Cl2 followed by trituration with hexane containing 1% of MeOH to give 0.245 g (81%) of the title compound as a white solid.

Workup

  1. customAlternative preparation
  2. customThe mixture was degassed with N2
  3. customThe reaction mixture was degassed again with N2
  4. temperaturecooled to ambient temperature
  5. additiondiluted with EtOAc
  6. washThe mixture was washed with water and brine
  7. dry with materialthe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customto give the crude product as a brown solid
  11. customThe crude product was purified by chromatography on a silica gel column
  12. washeluted with 25% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-f49cec86f1374dc9b771344e9384ce40
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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