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

HRID 250729ノート

反応式

HRID 250729 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 8471Triethylamine溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-8b08fa5269ea49c69d026769159d5a0f
出典データセット
uspto-grants-2011_01
特許番号
US07863310B2

反応ノート

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