1-Octyne → HCID 25222178, compound

HRID 1967211Notes

Reaction equation

HRID 1967211 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4](OS(C2C=CC(C)=CC=2)(=O)=O)[CH:3]=1.[CH:19]#[C:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]C.[CH3:27]CCCCCC.CCOC(C)=O>>[CH3:27][C:4]1[CH:3]=[C:2]([C:1]#[C:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:7]=[CH:6][N:5]=1

Participants

4

Reactant 3

HCID 123701-OctyneHCID 21899848Ethylacetate heptaneHCID 86646621Toluene-4-sulfonic acid 6-methyl-pyrimidin-4-yl ester

Product 1

HCID 25222178HCID 25222178, compound

Procedure

This product was prepared from toluene-4-sulfonic acid 6-methyl-pyrimidin-4-yl ester and 1-octyne following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/EtOAc 8:2; yield (37.6 mg, 40%); 1H NMR δ (CDCl3): 9.01 (s, 1H), 7.21 (s, 1H), 2.52 (s, 3H), 2.48 (t, J=7.23 Hz, 2H), 1.63 (p, J=7.17 Hz, 2H), 1.50-1.30 (m, 6H), 0.91 (t, J=7.25 Hz, 3H); LCMS m/z: 188.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (37.6 mg, 40%)

Sources & evidence

ORD record
ord-9528867b28894cea9286cbc4579f496f
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

Loading…