1-Ethynyl-4-methoxybenzene → 3-(4-Methoxy-phenyl-1-ethynyl)-pyridine

HRID 1967208Notes

Reaction equation

HRID 1967208 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]([O:26][CH3:27])=[CH:22][CH:21]=1)#[CH:19]>CCCCCCC.CCOC(C)=O>[CH3:27][O:26][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 2510201-Ethynyl-4-methoxybenzeneHCID 1712496HCID 1712496, compound

Product 1

HCID 112412523-(4-Methoxy-phenyl-1-ethynyl)-pyridine

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-methoxy-benzene following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/EtOAc 8:2; yield (83 mg, 80%); 1H NMR δ (CDCl3): 8.76-8.74 (m, 1H), 8.50-8.53 (m, 1H), 7.76-7.73 (m, 1H), 7.49-8.46 (m, 2H), 7.24-7.20 (m, 1H), 6.88-6.85 (m, 2H), 3.78 (s, 3H); LCMS m/z: 209.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (83 mg, 80%)

Sources & evidence

ORD record
ord-68ef6ad6af7546ebb3d4544768bf64ad
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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