N-Acetyl-O-p-toluenesulfonyl-2-aminophenol → N-[2-(4-Amino-phenylethynyl)-phenyl]-acetamide

HRID 451256Notes

Reaction equation

HRID 451256 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1OS(C1C=CC(C)=CC=1)(=O)=O)(=[O:3])[CH3:2].[C:22]([C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1)#[CH:23]>CCCCCCC.CCOC(C)=O>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:22]#[C:23][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:1](=[O:3])[CH3:2])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 572553N-Acetyl-O-p-toluenesulfonyl-2-aminophenolHCID 37600254-Ethynylaniline

Product 1

HCID 25221494N-[2-(4-Amino-phenylethynyl)-phenyl]-acetamide

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 2-acetylamino-phenyl ester and 4-ethynyl-phenylamine following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane/EtOAc 9:1; yield (47 mg, 50%); 1H NMR δ (CDCl3): 8.39 (d, J=8.52 Hz, 1H), 7.9 (br s, 1H), 7.59-7.67 (m, 2H), 7.58-7.52 (m, 2H), 7.41-7.35 (m, 2H), 7.02 (t, J=7.21 Hz, 1H), 3.82 (b, 2H), 2.21 (s, 3H); LCMS m/z: 250.

Workup

  1. customyield (47 mg, 50%)

Sources & evidence

ORD record
ord-11b31e45c10146a1a9d3336d7ea5a7c4
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

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