HCID 1712496, compound → HCID 25222176, compound

HRID 1967209Notes

Reaction equation

HRID 1967209 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](OS(C2C=CC(C)=CC=2)(=O)=O)[CH:2]=1.[C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1)#[CH:19]>CCCCCCC.CCOC(C)=O>[F:29][C:26]([F:27])([F:28])[C:23]1[CH:24]=[CH:25][C:20]([C:18]#[C:19][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 1712496HCID 1712496, compoundHCID 43482951-Ethynyl-4-(trifluoromethyl)benzene

Product 1

HCID 25222176HCID 25222176, compound

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid pyridin-3-yl ester and 1-ethynyl-4-trifluoromethyl-benzene following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/EtOAc 8:2; yield (87 mg, 70%); 1H NMR δ (CDCl3): 8.75-8.73 (m, 1H), 8.49-8.52 (m, 1H), 7.76-7.73 (m, 1H), 7.49-8.46 (m, 2H), 7.23-7.19 (m, 1H), 6.87-6.84 (m, 2H); LCMS m/z: 247.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (87 mg, 70%)

Sources & evidence

ORD record
ord-8aae733c888b49da8aad4f8b8e811f5c
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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