Methyl morpholine oxide → 2-Bromoimidazo[5,1-b]thiazole-7-carbaldehyde

HRID 1444193Notes

Reaction equation

HRID 1444193 reaction equation
[Br:1][C:2]1[S:6][C:5]2=[C:7]([CH2:10][OH:11])[N:8]=[CH:9][N:4]2[CH:3]=1.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Br:1][C:2]1[S:6][C:5]2=[C:7]([CH:10]=[O:11])[N:8]=[CH:9][N:4]2[CH:3]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 591684062-Bromo-7-hydroxymethylimidazo[5,1-b]thiazole

Product 1

HCID 115287442-Bromoimidazo[5,1-b]thiazole-7-carbaldehydeYield 21%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Dried 4A molecular sieves (40 mg) and tetra-n-propylammonium perruthenate (16 mg, 0.05 mmol) were added to a solution of 2-bromo-7-hydroxymethylimidazo[5,1-b]thiazole (53 mg, 0.23 mmol) and N-methylmorpholine-N-oxide (92 mg, 0.79 mmol) in dichloromethane (2 ml), and the mixture was stirred at room temperature for 3 days. The reaction solution was purified by column chromatography on silica gel (ethyl acetate:methanol=60:1) to give 2-bromoimidazo[5,1-b]thiazole-7-carbaldehyde (11 mg, 21%) as a white solid.

Workup

  1. customThe reaction solution was purified by column chromatography on silica gel (ethyl acetate:methanol=60:1)

Sources & evidence

ORD record
ord-26e0f52d712142ab8df2a0f7f16a38df
Source dataset
uspto-grants-2010_02
Patent number
US07662841B2

Reaction notes

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