Triethylamine → HCID 69291529, compound

HRID 2224369Notes

Reaction equation

HRID 2224369 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:20]=1)[CH2:7][N:8]([C:12]1[C:17]([CH:18]=[CH2:19])=[CH:16][CH:15]=[CH:14][N:13]=1)[C:9](=[O:11])[CH3:10].C(N(CC)CC)C>CN(C=O)C.C([O-])(O)=O.[Na+].[Pd](Cl)Cl>[C:9]([N:8]1[C:12]2[N:13]=[CH:14][CH:15]=[CH:16][C:17]=2[CH:18]=[CH:19][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:20][C:6]=2[CH2:7]1)(=[O:11])[CH3:10]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 59717607HCID 59717607, compound

Product 1

HCID 69291529HCID 69291529, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred mixture of N-(5-Bromo-2-iodo-benzyl)-N-(3-vinyl-pyridin-2-yl)-acetamide E (60.0 mg, 0.13 mmol) and triethyl amine (55.0 μL, 0.39 mmol) in anhydrous DMF (1.4 mL) under argon was added Palladium dichloride (4.60 mg, 26 μmol). This mixture was heated at 65° C. for 1 h, cooled and diluted with saturated NaHCO3 solution (20 mL). The mixture was extracted with EtOAc (4×30 mL). The combined EtOAc extracts were washed with water (3×10 mL), brine (1×10 mL), dried (MgSO4), filtered and concentrated in vacuo. This was purified by a ISCO auto CombiFlash with a RediSep 4 g column, eluted with CH2Cl2-EtOAc, detected at 254 nM to give 33 mg of 78F in 77% yield. HPLC Rt=3.04 min (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm) LC/MS: M+H=329.

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted with EtOAc (4×30 mL)
  3. washThe combined EtOAc extracts were washed with water (3×10 mL), brine (1×10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThis was purified by a ISCO auto CombiFlash with a RediSep 4 g column
  8. washeluted with CH2Cl2-EtOAc

Sources & evidence

ORD record
ord-4279ac20a7084b59901a14a9b72d86c5
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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