1,2-Dimethoxyethane → HCID 123232876, compound

HRID 2209062Notes

Reaction equation

HRID 2209062 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C@@H:9]([C@H:11]2[CH2:15][NH:14][C:13](=[O:16])[CH2:12]2)[CH3:10])[C:5]2[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[N:19][C:4]=2[CH:3]=1.[CH3:28][O:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][C:35]=1[O:36][CH3:37].COCCOC.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH3:28][O:29][C:30]1[CH:31]=[C:32]([C:2]2[N:7]=[C:6]([O:8][C@@H:9]([C@H:11]3[CH2:15][NH:14][C:13](=[O:16])[CH2:12]3)[CH3:10])[C:5]3[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[N:19][C:4]=3[CH:3]=2)[CH:33]=[CH:34][C:35]=1[O:36][CH3:37]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 27347023,4-Dimethoxyphenylboronic acidHCID 123533406HCID 123533406, compound

Product 1

HCID 123232876HCID 123232876, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Into the solution of (R)-4-((R)-1-(6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 2.12 (267 mg, 0.65 mmol) and 3,4-dimethoxyphenylboronic acid (142 mg, 0.78 mmol) in 2:1 DME:water (10 ml) was added cesium carbonate (3 equiv), and PEPPSI-IPr catalyst (0.1 equiv). Mixture was refluxed for 3 h, cooled to room temperature, poured into water and extracted with ethyl acetate (100 mL). Separated organic layer was washed with Brine (2×50 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to yield residues which were purified by silica gel column chromatography to isolate (R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.08.

Workup

  1. temperatureMixture was refluxed for 3 h
  2. extractionextracted with ethyl acetate (100 mL)
  3. washSeparated organic layer was washed with Brine (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield residues which
  8. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-29b093d996d34acebf57c3c204672a78
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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