Triethylamine → HCID 57820004, compound

HRID 1714164Notes

Reaction equation

HRID 1714164 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:22])[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[O:10])=[CH:4][CH:3]=1.[C:23]([O:27][C:28](=[O:41])[NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH:36][C:37](=[O:40])[CH:38]=[CH2:39])([CH3:26])([CH3:25])[CH3:24].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[Cl-].[NH4+]>CN(C=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]>[C:23]([O:27][C:28](=[O:41])[NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH:36][C:37](=[O:40])/[CH:38]=[CH:39]/[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:22])[C:9](=[O:10])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 80271Tri-o-tolylphosphineHCID 20786195HCID 20786195, compoundHCID 57820077HCID 57820077, compound

Product 1

HCID 57820004HCID 57820004, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-Bromo-phenyl)-2-hydroxy-N-(4-trifluoromethyl-phenyl)-acetamide (8.0 g, 21.4 mmol), (2-acryloylamino-phenyl)-carbamic acid tert-butyl ester (6.2 g, 23.6 mmol), tri-o-tolyl-phosphine (1.0 g, 3.3 mmol), triethylamine (12 mL, 86 mmol), and Pd2(dba)3 (1.5 g, 1.6 mmol) in DMF (160 mL) was heated at 90 degrees Celcius overnight under nitrogen atmosphere. The mixture was poured into saturated ammonium chloride solution (300 mL) and extracted with ethyl acetate three times. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated, and purified by flash column chromatography (ethyl acetate/petroleum ether 1:2) to obtain a white solid (5.8 g, 49%).

Workup

  1. temperaturewas heated at 90 degrees Celcius overnight under nitrogen atmosphere
  2. extractionextracted with ethyl acetate three times
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (ethyl acetate/petroleum ether 1:2)

Sources & evidence

ORD record
ord-c48e60cff14649788998bafff9aa75ef
Source dataset
uspto-grants-2010_09
Patent number
US07795315B2

Reaction notes

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