Triethylamine → HCID 20498760, compound

HRID 2235433Notes

Reaction equation

HRID 2235433 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[CH2:5][N:6]([CH3:8])[CH3:7].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(CC)CC>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:17]([O:16][C:12](=[O:15])/[CH:13]=[CH:14]/[C:2]1[CH:11]=[CH:10][CH:9]=[C:4]([CH2:5][N:6]([CH3:8])[CH3:7])[CH:3]=1)[CH3:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 4341665(3-BROMOBENZYL)DIMETHYLAMINE

Product 1

HCID 20498760HCID 20498760, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A mixture of (3-bromo-benzyl)-dimethyl-amine (1.10 g), ethyl acrylate (0.8 ml; 7.7 mmol), tri-o-tolyl-phosphane (156 mg; 0.53 mmol), Pd(OAc)2 (40 mg; 0.16 mmol) and NEt3 (1.4 ml; 10 mmol) is heated under reflux for 8 h. The reaction mixture is evaporated and the residue is subjected to flash chromatography on silica gel eluting with CH2Cl2/MeOH (95:5) to give the compound (800 mg).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 8 h
  3. customThe reaction mixture is evaporated

Sources & evidence

ORD record
ord-e11fae9505704198aef0918ac4d7c27f
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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