1,2-Dimethoxyethane → HCID 18448299, compound

HRID 1269691Notes

Reaction equation

HRID 1269691 reaction equation
Br[C:2]1[C:3]([CH3:28])=[C:4]([N:8]([CH2:13][C:14]2[CH:26]=[CH:25][C:17](OCC(OCC)=O)=[C:16](C)[CH:15]=2)[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:6][CH:7]=1.[CH3:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C(=O)([O-])[O-:40].[Na+].[Na+].C[O:46][CH2:47][CH2:48][O:49][CH3:50]>O.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>[CH2:9]([N:8]([CH2:13][C:14]1[CH:15]=[CH:16][C:50]([O:49][CH2:48][C:47]([OH:40])=[O:46])=[C:25]([CH3:17])[CH:26]=1)[C:4]1[C:3]([CH3:28])=[C:2]([C:33]2[CH:34]=[CH:35][C:30]([CH3:29])=[CH:31][CH:32]=2)[CH:7]=[CH:6][CH:5]=1)[CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 58622888HCID 58622888, compound

Product 1

HCID 18448299HCID 18448299, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl (4-{[(3-bromo-2-methylphenyl)(butyl)amino]methyl}-2-methylphenoxy)acetate (90 mg, 0.2 mmol), 4-methylphenylboronic acid (32 mg, 0.23 mmol), tetrakis(triphenylphosphine)palladium (0) (5 mg, 4.32 mmol), sodium carbonate (55 mg, 0.52 mmol) in 1,2-dimethoxyethane (10 mL) and water (5 mL) was heated at 90° C. for 18 h under nitrogen. The reaction mixture was cooled and the solvents removed in vacuo. Purification by SPE (C18, 10 g) eluting with 20 mL each of 5%, 10%, 30%, 50% acetonitrile/water, acetonitrile, MeOH. Further purification with SPE (amino propyl, 10 g), eluted with CH2Cl2 (40 mL), CHCl3 (20 mL), ether (20 mL), EtOAc (40 mL), MeOH (20 mL), 10% NH3/MeOH (40 mL) afforded the title compound as a colourless oil (50 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvents removed in vacuo
  3. customPurification by SPE (C18, 10 g)
  4. washeluting with 20 mL each of 5%, 10%, 30%, 50% acetonitrile/water, acetonitrile, MeOH
  5. customFurther purification with SPE (amino propyl, 10 g)
  6. washeluted with CH2Cl2 (40 mL), CHCl3 (20 mL), ether (20 mL), EtOAc (40 mL), MeOH (20 mL), 10% NH3/MeOH (40 mL)

Sources & evidence

ORD record
ord-20fb9d8d196c41499d8a1862d3c04a4d
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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