Phenylacetylene → 1-Phenyl-2-(3-(isopropyl)amino-4-nitrophenyl)acetylene

HRID 250729Notes

Reaction equation

HRID 250729 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[C:9](Br)[CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])([CH3:3])[CH3:2].[C:15]1([C:21]#[CH:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:15]1([C:21]#[C:22][C:9]2[CH:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])[CH:10]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 249029775-Bromo-N-isopropyl-2-nitroaniline

Product 1

HCID 668688151-Phenyl-2-(3-(isopropyl)amino-4-nitrophenyl)acetyleneYield 85%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

Bubble nitrogen through a mixture of N-[isopropyl]2-nitro-5-bromoaniline (0.34 g, 1.31 mmol), phenylacetylene (0.20 g, 1.96 mmol), palladium(II) acetate (7.3 mg, 0.033 mmol) and triphenylphosphine (17 mg, 0.065 mmol) in triethylamine (5 ml) for 3 minutes, then heat at reflux for 1 hour. Cool to room temperature and concentrate under reduced pressure. Partition the residue between ethyl acetate and saturated aqueous sodium chloride, dry the organic phase over sodium sulfate, and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 9:1 hexane:ethyl acetate to provide the desired compound as a red solid (0.31 g, 85%).

Workup

  1. customBubble nitrogen
  2. temperatureheat
  3. temperatureat reflux for 1 hour
  4. concentrationconcentrate under reduced pressure
  5. customPartition the residue between ethyl acetate and saturated aqueous sodium chloride
  6. dry with materialdry the organic phase over sodium sulfate
  7. concentrationconcentrate under reduced pressure
  8. washeluting with 9:1 hexane

Sources & evidence

ORD record
ord-8b08fa5269ea49c69d026769159d5a0f
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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