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

HRID 1438654

반응식

HRID 1438654 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
110 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-c6a4bb16775f4311a54db4316066eb64
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622583B2

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