1-Heptyne → 3-Acetylamino-4-hept-1-ynyl-benzoic acid methyl ester

HRID 451258

Reaction equation

HRID 451258 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7](OS(C2C=CC(C)=CC=2)(=O)=O)=[C:6]([NH:21][C:22](=[O:24])[CH3:23])[CH:5]=1.[CH:26]#[C:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>CCCCCCC.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([C:26]#[C:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:6]([NH:21][C:22](=[O:24])[CH3:23])[CH:5]=1

Participants

4

Reactant 2

HCID 123501-HeptyneHCID 866466243-Acetylamino-4-(toluene-4-sulfonyloxy)-benzoic acid methyl ester

Product 1

HCID 252214963-Acetylamino-4-hept-1-ynyl-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from 3-acetylamino-4-(toluene-4-sulfonyloxy)-benzoic acid methyl ester and 1-heptyne following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane/EtOAc 8:2; yield (80 mg, 55%); 1H NMR δ (CDCl3): 8.96 (d, J=1.51 Hz, 1H), 7.92 (br s, 1H), 7.66 (dd, J=1.57, J=8.33 Hz, 1H), 7.38 (d, J=8.15 Hz, 1H), 3.89 (s, 3H), 2.53 (t, J=7.09 Hz, 2H), 2.21 (s, 3H), 1.63 (p, J=7.16 Hz, 2H), 1.48-1.3 (m, 4H), 0.92 (t, J=7.26 Hz, 3H); LCMS m/z: 287.

Workup

  1. customyield (80 mg, 55%)

Sources & evidence

ORD record
ord-0294fbefa42648c2869fb4dd0c384f4b
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Linked notes

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