Dimethylformamide → Methyl 3-amino-5-methylthieno[2,3-b]pyridine-2-carboxylate

HRID 442774

반응식

HRID 442774 반응식
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[C:4](C)[N:3]=1.[C:11]([O:15][CH3:16])(=[O:14])[CH2:12][SH:13].[OH-].[K+].[CH3:19]N(C=O)C>O>[NH2:9][C:8]1[C:7]2[C:2](=[N:3][CH:4]=[C:5]([CH3:19])[CH:6]=2)[S:13][C:12]=1[C:11]([O:15][CH3:16])=[O:14]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 16907Methyl ThioglycolateHCID 5204002-Chloro-6-methylpyridine-3-carbonitrile

생성물 1

HCID 18796992Methyl 3-amino-5-methylthieno[2,3-b]pyridine-2-carboxylate수율 79%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

2-Chloro-3-cyano-6-methyl pyridine (1.5 g, 9.8 mmol) and methyl thioglycolate (0.88 mL, 9.8 mmol) were dissolved in DMF (7 mL). To the solution was added 1.0 g KOH in 5 mL H2O over 30 min. The reaction was then quenched by the addition of ice water, and the product collected by filtration to yield 1.72 g (79%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 2.88 (s, 3H), 3.91 (s, 3H), 5.90 (br s, 2H), 7.17 (d, 1H), 7.82 (d, 1H),

후처리

  1. customThe reaction was then quenched by the addition of ice water
  2. filtrationthe product collected by filtration

출처 및 근거

ORD 기록
ord-d3ee6c207b7943b98275390a5337eebe
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891882

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