(4-Methoxy-3-methylphenyl)boronic acid → HCID 71226501, compound

HRID 713445Notes

Reaction equation

HRID 713445 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][C:4]=1[CH3:12].[CH2:13]([O:15][C:16](=[O:33])[CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([C:24](SC2C=CC=CC=2)=[O:25])[CH2:20][CH2:19]1)[CH3:14]>COCCOC.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].S1C=CC=C1C([O-])=O.[Cu+]>[CH2:13]([O:15][C:16](=[O:33])[CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([C:24](=[O:25])[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:12])[CH:5]=2)[CH2:20][CH2:19]1)[CH3:14]

Participants

7

Reactant 2

HCID 2773487(4-Methoxy-3-methylphenyl)boronic acidHCID 89389237HCID 89389237, compound

Product 1

HCID 71226501HCID 71226501, compoundYield 46.2%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 11194830Cuprous 2-thiophenecarboxylateCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-methoxy-3-methyl phenylboronic acid (0.32 g, 1.95 mmol), ligand TFP (0.06 g, 0.26 mmol), Pd2dba3 (0.12 g, 0.13 mmol), copper (I) thiophene-2-carboxylate (0.37 g, 2.0 mmol) was added a solution of (4-phenylsulfanylcarbonyl-piperidin-1-yl)-acetic acid ethyl ester (0.4 g, 1.3 mmol) in 6 mL of DME. It was stirred at RT for 16 hours, the reaction mixture was diluted with ethyl acetate, filtered through celite then concentrated in vacuo. Purification by flash chromatography gave the title compound (0.2 g, 0.6 mmol). MS (ESI) m/z 319.8 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.36 min.

Workup

  1. filtrationfiltered through celite
  2. concentrationthen concentrated in vacuo
  3. customPurification by flash chromatography

Sources & evidence

ORD record
ord-095f9cee8b4c400db75416dcf43a063c
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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