Dimethylformamide → HCID 22730625, compound

HRID 1785829Notes

Reaction equation

HRID 1785829 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=2)=[C:6]([O:20][CH3:21])[CH:5]=1.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.CN(C=[O:34])C>O.C(OCC)(=O)C>[CH3:21][O:20][C:6]1[CH:5]=[C:4]([CH2:3][C:2]([N:27]2[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]2)=[O:34])[CH:9]=[CH:8][C:7]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 531671-MethylpiperazineHCID 11531974HCID 11531974, compound

Product 1

HCID 22730625HCID 22730625, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 328A (213 mg, 0.5 mmol), 1-methylpiperazine (2.5 mmol), and bis(tricyclohexylphosphine)palladium chloride (0.0025 mmol) in DMF (1.5 mL) and water (0.25 mL) was heated to 80° C. for 8 hours, diluted with ethyl acetate (100 mL), washed with water (45 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silical gel with 2-10% methanol/dichloromethane to provide the desired product.

Workup

  1. washwashed with water (45 mL) and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silical gel with 2-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-7f5efceca31e4d5698156ae99f8c7ee1
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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