Azidotrimethylsilane → 6-Azido-pyridine-2-carboxylic acid methoxy-methyl-amide

HRID 419212

Reaction equation

HRID 419212 reaction equation
[CH3:1][O:2][N:3]([CH3:13])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8](F)[N:7]=1)=[O:5].[N:14]([Si](C)(C)C)=[N+:15]=[N-:16]>CN(C=O)C.ClCCl>[CH3:1][O:2][N:3]([CH3:13])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N:14]=[N+:15]=[N-:16])[N:7]=1)=[O:5]

Participants

5

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 597006206-fluoro-N-methoxy-N-methylpicolinamide

Product 1

HCID 579422046-Azido-pyridine-2-carboxylic acid methoxy-methyl-amideYield 25%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-fluoro-pyridine-2-carboxylic acid methoxy-methyl-amide (1.19 g, 6.47 mmol) and azido-trimethylsilane (2.0 g, 16.8 mmol) in DMF (10 mL) was stirred at 110° C. for 72 h. The reaction mixture was diluted with 50 mL of dichloromethane and washed with water (3×50 mL). The organic layer was separated, evaporated to dryness, and subjected to column chromatography (SiO2, 40% EtOAc-hexanes) to obtain 6-azido-pyridine-2-carboxylic acid methoxy-methyl-amide (0.335 g) in 25% yield. ESMS m/z (relative intensity): 208 (M+H)+ (100).

Workup

  1. washwashed with water (3×50 mL)
  2. customThe organic layer was separated
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-54e4ba292a5c43fba83ab73e8e8a8708
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Linked notes

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