Sodium Iodide → 2-Amino-3-benzoyl-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 430622노트

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HRID 430622 반응식
[NH2:1][C:2]1[S:10][C:5]2[CH2:6][NH:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CI.[C:21](=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[NH2:1][C:2]1[S:10][C:5]2[CH2:6][N:7]([CH3:21])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:11](=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15434454(2-Amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)phenylmethanone

생성물 1

HCID 154344492-Amino-3-benzoyl-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine수율 77%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
65 °C

실험 절차

2-Amino-3-benzoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (2 mmol), as prepared in Example 8, and methyl iodide (3 mmol) were dissolved in dry dimethyformamide (20 mL). Finely ground anhydrous potassium carbonate (1.9 g) and sodium iodide (0.2 g) were added to the solution and the resulting mixture was warmed to 65° C. overnight under nitrogen. After this period (TLC control), the reaction mixture was cooled, diluted with water, extracted with diethyl ether (3×50 mL), and dried on sodium sulfate. The crude product was isolated and then purified by column chromatography eluting with ethyl acetate and petroleum ether solutions to give the desired compound. (m.p. 164-165° C.; 77% yield).

후처리

  1. waitAfter this period (TLC control)
  2. temperaturethe reaction mixture was cooled
  3. extractionextracted with diethyl ether (3×50 mL)
  4. customdried on sodium sulfate
  5. customThe crude product was isolated
  6. custompurified by column chromatography
  7. washeluting with ethyl acetate and petroleum ether solutions

출처 및 근거

ORD 기록
ord-0e2708f340294bf081c6ad26630130f8
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323214B1

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