Morpholine → HCID 72195896, compound

HRID 626348Notes

Reaction equation

HRID 626348 reaction equation
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.Br[C:48]1[CH:49]=[C:50]([C:58]([NH:60][C:61]2[CH:62]=[C:63](/[CH:67]=[CH:68]/[C:69]([O:71]CC)=[O:70])[CH:64]=[CH:65][CH:66]=2)=[O:59])[C:51]2[C:56]([CH:57]=1)=[CH:55][CH:54]=[CH:53][CH:52]=2.[NH:74]1[CH2:79][CH2:78][O:77][CH2:76][CH2:75]1.CC(C)([O-])C.[K+]>O.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].CN(C=O)C>[N:74]1([C:48]2[CH:49]=[C:50]([C:58]([NH:60][C:61]3[CH:62]=[C:63](/[CH:67]=[CH:68]/[C:69]([OH:71])=[O:70])[CH:64]=[CH:65][CH:66]=3)=[O:59])[C:51]3[C:56]([CH:57]=2)=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH2:79][CH2:78][O:77][CH2:76][CH2:75]1

Participants

8

Reactant 4

HCID 8083MorpholineHCID 634876Binap, (A+-)-HCID 23665647Potassium tert-butoxideHCID 90057966HCID 90057966, compound

Product 1

HCID 72195896HCID 72195896, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A Biotage Process Vial (5-20 mL) was charged with (BINAP) (0.47 mmol), Pd2(dba)3 (0.11 mmol), ethyl(E)-3-[3-[(3-bromonaphthalene-1-carbonyl)amino]phenyl]prop-2-enoate (23) (1.17 mmol), morpholine (3.53 mmol), and potassium tertbutoxide (2.35 mmol). The vial was charged with DMF (5 mL) and irradiated at 100-130° C. for 1 h, using the microwave reactor Smith Synthesizer. After irradiation, the sample was cooled and diluted with water and extracted with ethyl acetate (3×50 mL). The organic layer was washed with water, brine and dried over Na2SO4 and the solvent evaporated to dryness to afford crude 28, which was purified by preparative HPLC.

Workup

  1. customirradiated at 100-130° C. for 1 h
  2. customAfter irradiation
  3. temperaturethe sample was cooled
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent evaporated to dryness
  8. customto afford crude 28, which
  9. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-0ed65d8aff224dc6976252524a283940
Source dataset
uspto-grants-2016_04
Patent number
US09309187B2

Reaction notes

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