Triethylamine → HCID 59238275, compound

HRID 220187Notes

Reaction equation

HRID 220187 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:13]1[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=1)[CH2:5][CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH3:12].[C:21]([O:25][C:26](=[O:39])[NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][C:35](=[O:38])[CH:36]=[CH2:37])([CH3:24])([CH3:23])[CH3:22].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]>[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:13]1[CH:18]=[CH:17][C:16](/[CH:37]=[CH:36]/[C:35](=[O:38])[NH:34][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[NH:27][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:39])=[CH:15][CH:14]=1)[CH2:5][CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH3:12]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 80271Tri-o-tolylphosphineHCID 20786195HCID 20786195, compoundHCID 59238292HCID 59238292, compound

Product 1

HCID 59238275HCID 59238275, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-bromo-phenyl)-4-(1-methyl-pyrrolidin-2-yl)-butyric acid methyl ester (2.27 g, 6.67 mmol), (2-acryloylamino-phenyl)-carbamic acid tert-butyl ester (2 g, 7.2 mmol), Pd2(dba)3 (160 mg, 0.175 mmol), tri-o-tolylphosphine (160 mg, 0.526 mmol) and triethylamine (1.6 g, 15.8 mmol) in DMF (12 mL) was stirred at 100 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 (80 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated in vacuo, and purified by flash column chromatography to obtain pale yellow solid. (1.74 g, 50%). MS: calc'd 522 (MH+), exp 522 (MH+).

Workup

  1. extractionextracted with ethyl acetate (80 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 pale yellow solid

Sources & evidence

ORD record
ord-fa4428e3b0ed4f86a156318584cd71ba
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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