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

HRID 250729노트

반응식

HRID 250729 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 11776Triphenylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 8471Triethylamine용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-8b08fa5269ea49c69d026769159d5a0f
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863310B2

반응 노트

불러오는 중…