Water → 4-hydroxy-3-methoxy-N-(3-phenylphenyl)phenylacetamide

HRID 7065

Reaction equation

HRID 7065 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14](I)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:19][CH3:20].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCCC1.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>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:19][CH3:20]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 120966604-hydroxy-N-(3-iodophenyl)-3-methoxyphenylacetamide

Product 1

HCID 120966624-hydroxy-3-methoxy-N-(3-phenylphenyl)phenylacetamideYield 82.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 1 (500 mg), phenylboronic acid (300 mg), tetrakis(triphenylphosphine)palladium (0) (150 mg) are dissolved in tetrahydrofuran (20 ml), and thereto are added cesium carbonate (850 mg) and water (10 ml). The mixture is heated under reflux for 18 hours under argon atmosphere. The reaction solution is extracted with ethyl acetate, and the organic layer is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (360 mg).

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 18 hours under argon atmosphere
  3. extractionThe reaction solution is extracted with ethyl acetate
  4. dry with materialthe organic layer is dried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9e05febe729d405e925148c7270b09cc
Source dataset
uspto-grants-2006_08
Patent number
US07084176B2

Linked notes

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