Methyl iodide → 1-(4-Methyl-5-methylsulfanyl-3-pyridin-3-yl-thiophen-2-yl)-propan-1-one

HRID 6852

반응식

HRID 6852 반응식
O=[C:2]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][C:4]#N.[C:12](=[S:14])=[S:13].Br[CH2:16][C:17](=[O:20])[CH2:18][CH3:19].[CH3:21]I.[NH4+].[Cl-]>CN(C=O)C>[CH3:4][C:3]1[C:2]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)=[C:16]([C:17](=[O:20])[CH2:18][CH3:19])[S:13][C:12]=1[S:14][CH3:21]

참가 물질

7

반응물 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 131561-Bromo-2-butanoneHCID 25517Ammonium ChlorideHCID 157315343-Oxo-3-(3-pyridinyl)propanenitrile

생성물 1

HCID 220190381-(4-Methyl-5-methylsulfanyl-3-pyridin-3-yl-thiophen-2-yl)-propan-1-one수율 32.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a solution of 3-oxo-3-pyridin-3-yl-propionitrile (11.9 mmol) in DMF (100 mL) was added CS2 (0.90 ml, 15.0 mmol) at 0° C. The reaction was stirred at 0° C. for 45 minutes under nitrogen then 1-bromo-butan-2-one (1.79 g, 11.8 mmol) was added via a syringe at 0° C. The reaction was stirred for another 30 minutes then methyl iodide (1.69 g, 11.8 mmol) was added via syringe at 0° C. The resulting mixture was stirred for another 30 minutes then warmed to ambient temperature and poured into saturated aqueous NH4Cl solution (300 mL). The solution was extracted with ethyl acetate (200 mL×3) and the combined organic layers were dried over Na2SO4 then concentrated in vacuo. Purification by chromatography (Silica Gel, 3:1 hexanes:ethyl acetate) afforded 1.05 g desired product. 1H NMR (CDCl3): δ 8.8 (d, 1H), 8.6 (s, 1H), 7.8 (d, 1H), 7.5 (dd, 1H), 2.8 (s, 3H), 2.3 (q, 2H), 1.0 (t, 3H).

후처리

  1. stirringThe reaction was stirred for another 30 minutes
  2. stirringThe resulting mixture was stirred for another 30 minutes
  3. temperaturethen warmed to ambient temperature
  4. extractionThe solution was extracted with ethyl acetate (200 mL×3)
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. concentrationthen concentrated in vacuo
  7. customPurification by chromatography (Silica Gel, 3:1 hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-b2ea8994468d4030884c9f6a18eafa8c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084159B2

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