Cesium carbonate → (S)-3-(4-{2-[4-(2-Methoxy-ethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy}-phenyl)-hex-4-ynoic acid ethyl ester

HRID 2272834Notes

Reaction equation

HRID 2272834 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][C@@H:6]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]3[N:22]([N:24]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=4)[N:26]=3)[CH:23]=2)=[CH:12][CH:11]=1)[C:7]#[C:8][CH3:9])[CH3:2].Br[CH2:36][CH2:37][O:38][CH3:39].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:34])[CH2:5][C@@H:6]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]3[N:22]([N:24]=[C:25]([C:27]4[CH:28]=[CH:29][C:30]([O:33][CH2:36][CH2:37][O:38][CH3:39])=[CH:31][CH:32]=4)[N:26]=3)[CH:23]=2)=[CH:12][CH:11]=1)[C:7]#[C:8][CH3:9])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 136992561(S)-3-{4-[2-(4-Hydroxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester

Product 1

HCID 118129985(S)-3-(4-{2-[4-(2-Methoxy-ethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy}-phenyl)-hex-4-ynoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution (S)-3-{4-[2-(4-hydroxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester (0.250 g, 0.585 mmol) and 1-bromo-2-methoxy-ethane (0.22 mL, 2.34 mmol) in acetonitrile (10 mL) is added cesium carbonate (0.381 g, 1.17 mmol) at room temperature and the reaction mixture is stirred at room temperature overnight. The reaction mixture is filtered through diatomaceous earth and washed with EtOAc (20 mL), and the filtrate is concentrated to dryness. The residue is dissolved in EtOAc (30 mL), washed with water (2×30 mL), brine solution (30 mL), dried over sodium sulphate, and evaporated under reduced pressure. The crude compound is purified by silica gel (combiflash purifier) and is eluted with 17-19% EtOAc in hexane to give the title compound as a white semi solid (0.190 g, 64%). LCMS m/z 514 (M+H)+.

Workup

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. washwashed with EtOAc (20 mL)
  3. concentrationthe filtrate is concentrated to dryness
  4. dissolutionThe residue is dissolved in EtOAc (30 mL)
  5. washwashed with water (2×30 mL), brine solution (30 mL)
  6. dry with materialdried over sodium sulphate
  7. customevaporated under reduced pressure
  8. customThe crude compound is purified by silica gel (combiflash purifier)
  9. washis eluted with 17-19% EtOAc in hexane

Sources & evidence

ORD record
ord-2171cea8d0b44ed3861e82101131b90b
Source dataset
uspto-grants-2015_09
Patent number
US09120793B2

Reaction notes

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