7-Hydroxymethyl-8-methoxy-2-(2-trimethylsilanyl-ethoxymethyl)-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one → 8-Methoxy-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridine-7-carbaldehyde

HRID 1037311Notes

Reaction equation

HRID 1037311 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]2[C:9](=[O:20])[N:10]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[N:11]=[C:5]2[C:4]=1[O:21][CH3:22]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:22][O:21][C:4]1[C:5]2[N:6]([C:9](=[O:20])[N:10]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[N:11]=2)[CH:7]=[CH:8][C:3]=1[CH:2]=[O:1]

Participants

4

Reactant 1

HCID 670678957-Hydroxymethyl-8-methoxy-2-(2-trimethylsilanyl-ethoxymethyl)-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one

Product 1

HCID 866710388-Methoxy-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridine-7-carbaldehydeYield 94.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 7-hydroxymethyl-8-methoxy-2-(2-trimethylsilanyl-ethoxymethyl)-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one (1.23 g, 3.78 mmol) in DCM (100 mL) was added manganese dioxide (3.30 g, 37.8 mmol). After 16 hours, the reaction mixture was filtered through Celite®. The filtrate was evaporated to dryness to afford the title compound (1.15 g, 94%) as a pale yellow solid. LCMS (Method A): RT=4.52 min, [M+Na]+=346.

Workup

  1. filtrationthe reaction mixture was filtered through Celite®
  2. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-7c490c7d4aff420d8bd676f57eb5c30a
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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