Triethylamine → HCID 67230511, compound

HRID 220197Notes

Reaction equation

HRID 220197 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]([C:16]1[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=1)[CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH3:2].[C:24]([O:28][C:29](=[O:42])[NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH:37][C:38](=[O:41])[CH:39]=[CH2:40])([CH3:27])([CH3:26])[CH3:25].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[NH4+].[Cl-]>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]>[CH2:1]([O:3][C:4](=[O:23])[CH:5]([C:16]1[CH:21]=[CH:20][C:19]([CH:40]=[CH:39][C:38](=[O:41])[NH:37][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[NH:30][C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:42])=[CH:18][CH:17]=1)[CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH3:2]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 80271Tri-o-tolylphosphineHCID 20786195HCID 20786195, compoundHCID 592383032-(4-Bromo-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester

Product 1

HCID 67230511HCID 67230511, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-Bromo-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester (4.5 g, 11.22 mmol), (2-acryloylamino-phenyl)-carbamic acid tert-butyl ester (3.1 g, 11.78 mmol), Pd2(dba)3 (839 mg, 0.92 mmol), tri-o-tolylphosphine (546 mg, 1.79 mmol) and triethylamine (4.53 g, 44.88 mmol) in DMF (50 mL) was stirred at 110 degrees Celsius under N2 for 4 hours. After cooling to room temperature, the mixture was poured into a saturated aqueous solution of NH4Cl, and extracted with ethyl acetate (200 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated in vacuo, and purified by flash column chromatography to obtain a pale yellow solid. (2.63 g, 42%). MS: calc'd 583 (MH+), exp 583 (MH+).

Workup

  1. extractionextracted with ethyl acetate (200 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by flash column chromatography
  7. customto obtain a pale yellow solid

Sources & evidence

ORD record
ord-4d2860a473f6453683f8cdc5ce3e304b
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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