HCID 69434808, compound → HCID 69435422, compound

HRID 1890634Notes

Reaction equation

HRID 1890634 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]3[C:29]4=[N:30][C:31]([CH3:35])=[CH:32][C:33]([CH3:34])=[C:28]4[N:27]=[C:26]3[CH2:36][CH3:37])[CH:19]=2)[OH:17])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH2:36]([C:26]1[N:25]([CH2:24][C:20]2[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=2)[C:16]([C:13]2[CH:12]=[CH:11][C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3])=[CH:15][CH:14]=2)=[O:17])[C:29]2=[N:30][C:31]([CH3:35])=[CH:32][C:33]([CH3:34])=[C:28]2[N:27]=1)[CH3:37]

Participants

4

Reactant 1

HCID 69434808HCID 69434808, compound

Product 1

HCID 69435422HCID 69435422, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

[4-(tert-Butyldimethylsilyloxymethyl)phenyl][3-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)phenyl]methanol (0.923 g, 1.78 mmol) obtained in Step 3 was dissolved in chloroform (20 mL), and Manganese(IV) oxide (3.11 g, 35.8 mmol) was added to the solution, followed by stirring overnight. The unsoluble material was filtered out through Celite, and the filtrate was combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1) to obtain {4-[3-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)benzoyl]benzyloxy}-tert-butyldimethylsilane (0.898 g, yield 98%).

Workup

  1. filtrationThe unsoluble material was filtered out through Celite
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-73f58c1a7a5541f39c86a7220e0ef5b7
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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