4-Ethynylaniline → HCID 25222181, compound

HRID 1967215Notes

Reaction equation

HRID 1967215 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3](OS(C2C=CC(C)=CC=2)(=O)=O)[CH:2]=1.[C:22]([C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1)#[CH:23]>CCCCCCC.CCOC(C)=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:23]#[C:22][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 37600254-EthynylanilineHCID 86646622HCID 86646622, compound

Product 1

HCID 25222181HCID 25222181, compound

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid quinolin-3-yl ester and 4-ethynyl-phenylamine following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/EtOAc 6:4; yield (120 mg, 98%); 1H NMR δ (CDCl3): 8.98 (s, 1H), 8.34 (s, 1H), 8.21 (d, J=8.60 Hz, 1H), 7.87-7.71 (d m, 2H), 7.68-7.57 (m, 1H), 7.40 (d, J=8.36 Hz, 2H), 6.67 (d, J=8.38 Hz, 2H), 4.46 (br s, 2H); LCMS m/z: 244.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (120 mg, 98%)

Sources & evidence

ORD record
ord-65b6fd947a4442dc876d37fa37c4d544
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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