7-[[5-(t-Butyldimethylsilyloxymethyl)pyridin-3-yl]hydroxymethyl]imidazo[5,1-b]thiazole → 7-[5-(t-Butyldimethylsilyloxymethyl)pyridin-3-yl]carbonyl imidazo[5,1-b]thiazole

HRID 1072332Notes

Reaction equation

HRID 1072332 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]([OH:25])[C:17]2[N:18]=[CH:19][N:20]3[CH:24]=[CH:23][S:22][C:21]=23)[CH:13]=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>ClCCl.[O-2].[O-2].[Mn+4]>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([C:16]([C:17]2[N:18]=[CH:19][N:20]3[CH:24]=[CH:23][S:22][C:21]=23)=[O:25])[CH:13]=[N:14][CH:15]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 223903777-[[5-(t-Butyldimethylsilyloxymethyl)pyridin-3-yl]hydroxymethyl]imidazo[5,1-b]thiazole

Product 1

HCID 223902847-[5-(t-Butyldimethylsilyloxymethyl)pyridin-3-yl]carbonyl imidazo[5,1-b]thiazoleYield 89.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (1.43 g) was added to a solution of 803 mg of 7-[[5-(t-butyldimethylsilyloxymethyl)-pyridin-3-yl]hydroxymethyl]imidazo[5,1-b]thiazole in 10 ml of dichloromethane, and the mixture was stirred at room temperature for 16 hr. The reaction solution was filtered through Celite, followed by washing with dichloromethane. The filtrate was concentrated under the reduced pressure to give 712 mg of 7-[5-(t-butyldimethylsilyloxymethyl)pyridin-3-yl]carbonyl imidazo[5,1-b]thiazole.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washby washing with dichloromethane
  3. concentrationThe filtrate was concentrated under the reduced pressure

Sources & evidence

ORD record
ord-20d8ab6d72b540d5b289ff25c300ee82
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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