Morpholine → 4-{5-(2,4-dimethylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}nitrobenzene

HRID 618322Notes

Reaction equation

HRID 618322 reaction equation
[CH3:1][C:2]1[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][C:3]=1[C:4]([C:6]1[N:10]([CH3:11])[C:9]([CH:12]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=2F)C(OCC=C)=O)=[CH:8][CH:7]=1)=[O:5].N1CCOCC1>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][C:3]=1[C:4]([C:6]1[N:10]([CH3:11])[C:9]([CH2:12][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[CH:8][CH:7]=1)=[O:5]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 23285845Allyl 2-[5-(2,4-dimethylbenzoyl)-1-methylpyrrol-2-yl)-2-(2-fluoro-4-nitrophenyl)-acetate

Product 1

HCID 232857664-{5-(2,4-dimethylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}nitrobenzeneYield 98.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl 2-[5- (2,4-dimethylbenzoyl)-1-methylpyrrol-2-yl)-2-(2-fluoro-4-nitrophenyl)acetate (3.6 g, 7.99 mmol) [prepared as described in Example 6, Step (d)] in anhydrous THF (40 ml) was added morpholine (6.99 ml, 79.90 mmol) and tetrakis-(triphenylphosphine) palladium (9 mg, 0.008 mmol)). After 1.5 h, the solvent was evaporated and the residue was partitioned between ether and IN NaHSO4. The organic layer was separated, dried over magnesium sulfate, and concentrated to dryness. Purification by column chromatography (ethyl acetate/hexane) gave 4-[5-(2,4-dimethylbenzoyl)-1-methyl-pyrrol-2-yl-methyl)nitrobenzene (2.73 g, 93%) as a pale yellow oil. ##STR37##

Workup

  1. customthe solvent was evaporated
  2. customthe residue was partitioned between ether and IN NaHSO4
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customPurification by column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3236a72bf50146f1ae137e0c31bc6b5c
Source dataset
uspto-grants-1999_09
Patent number
US05952368

Reaction notes

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