Toluene → HCID 21830740, compound

HRID 1600974Notes

Reaction equation

HRID 1600974 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([C:11]1[CH:28]=[C:27](Br)[CH:26]=[CH:25][C:12]=1[O:13][CH2:14][CH:15]([OH:24])[CH2:16][CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)(=[O:10])[CH3:9].C1(B(O)O)C=CC=CC=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.C(O)C>[C:8]([C:11]1[CH:28]=[C:27]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:26]=[CH:25][C:12]=1[O:13][CH2:14][CH:15]([OH:24])[CH2:16][CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)(=[O:10])[CH3:9]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 21830684HCID 21830684, compound

Product 1

HCID 21830740HCID 21830740, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

Prepared according to the method described in Example 33a) from toluene (7.5 ml), (±)-1-(2-acetyl-4-bromophenoxy)-4-(3-pyridyl)-2-butanol (0.134 g), benzeneboronic acid (0.07 g), aqueous sodium carbonate (2 M, 1 ml), ethanol (2.5 ml) and tetrakis(triphenylphosphine)palladium(0) (0.02 g) with heating at reflux for 3 hours. After work up the residue was purified by column chromatography over silica eluting with ethanol:dichloromethane (5:95) to give the title compound as an oil (0.070 g).

Workup

  1. customPrepared
  2. temperaturewith heating
  3. temperatureat reflux for 3 hours
  4. customAfter work up the residue was purified by column chromatography over silica eluting with ethanol:dichloromethane (5:95)

Sources & evidence

ORD record
ord-85e15d7bff0e49728928134623fae005
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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