Diisopropylethylamine → HCID 18512252, compound

HRID 1370783Notes

Reaction equation

HRID 1370783 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Br[CH2:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=1>CN(C=O)C.C(OCC)C>[CH2:1]([N:8]([CH2:29][C:30]1[CH:31]=[CH:32][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:38][CH:39]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 256687Methyl 4-(bromomethyl)benzoateHCID 18512106HCID 18512106, compound

Product 1

HCID 18512252HCID 18512252, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

The product from Example 6A (0.92 g, 3.8 mmoles) and diisopropylethylamine (1.7 mL, 9.5 mmoles) in DMF (9.5 mL) were treated with methyl 4-(bromomethyl)benzoate (0.74 g, 7.6 mmoles) and heated for 18 hours at 90° C. After cooling to room temperature, the mixture was diluted with diethyl ether (200 mL). The mixture was washed with saturated ammonium chloride (200 mL), water (2×200 mL), brine (150 mL), dried (Na2SO4), filtered and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 10:1→4:1 hexanes:ethyl acetate) to provide the title compound as a yellow solid (1.26 g, 85%).

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe mixture was washed with saturated ammonium chloride (200 mL), water (2×200 mL), brine (150 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (silica gel, 10:1→4:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-4a861b3ce0ce4673b8230ecef6f2f3db
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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