Cesium carbonate → (S)-3-(4-{2-[4-(3-Hydroxy-3-methyl-butoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-6-yl methoxy}-phenyl)-hex-4-ynoic acid ethyl ester

HRID 2272835Notes

Reaction equation

HRID 2272835 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][C:38]([CH3:41])([OH:40])[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][C:38]([OH:40])([CH3:41])[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 106071724-Bromo-2-methylbutan-2-olHCID 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 118129976(S)-3-(4-{2-[4-(3-Hydroxy-3-methyl-butoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-6-yl methoxy}-phenyl)-hex-4-ynoic acid ethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (S)-3-{4-[2-(4-hydroxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester (0.2 g, 0.43 mmol) in acetonitrile (20 mL) is added 4-bromo-2-methyl-butan-2-ol (0.14 g, 0.87 mmol) and cesium carbonate (0.41 g, 1.2 mmol) and the reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is filtered and evaporated to dryness. The crude material is purified by silica gel chromatography (combiflash purifier 24 g redisep column) and is eluted with 15-20% EtOAc in hexane to give the title compound (0.23 g, 100%). LCMS m/z 542 (M+H)+.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated to dryness
  3. customThe crude material is purified by silica gel chromatography (combiflash purifier 24 g redisep column)
  4. washis eluted with 15-20% EtOAc in hexane

Sources & evidence

ORD record
ord-126887e2e6394d5e837a097c177a4ffc
Source dataset
uspto-grants-2015_09
Patent number
US09120793B2

Reaction notes

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