Methyl iodide → 3-Bromo-2-methylthieno(2,3-b)pyridine

HRID 226070

반응식

HRID 226070 반응식
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][CH:3]=1.O1CCC[CH2:12]1.C(NC(C)C)(C)C.[Li].CI>C1COCC1.C1CCCCC1>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[CH3:12]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 2899263-Bromothieno[2,3-b]pyridineHCID 68798419Lithium diisopropylamine mono(tetrahydrofuran)

생성물 1

HCID 688577263-Bromo-2-methylthieno(2,3-b)pyridine수율 45%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8078Cyclohexane용매

반응 조건

온도
-78 °C

실험 절차

500 mg of 3-Bromo-thieno[2,3-b]pyridine (3.70 mmol) is dissolved in 3 ml of dry THF and cooled to −78° C. 2.71 ml of lithium diisopropylamine mono (tetrahydrofuran) 1.5 M solution in cyclohexane (4.07) is added to the mixture at −78° C. and stirred at −78° C. for 20 min. 0.25 ml of methyl iodide (43.7 mmol) is added to the mixture and stirred at −78° C.→room temperature for 1 h. The reaction mixture is quenched with sat. NH4Cl and extracted with CH2Cl2. The separated CH2Cl2 is dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane:AcOEt=3:1) to give 382 mg of the title compound. Yield 45%. mass spectrum (m/e): 230 (M+1); 1H-NMR (CDCl3): 8.56 (dd, 1H, J=4.7 Hz, 1.5 Hz), 7.97 (dd, 1H, J=8.5 Hz, 1.5 Hz), 7.37 (dd, 1H, J=8.5 Hz, 4.7 Hz), 2.62 (s, 3H) ppm.

후처리

  1. stirringstirred at −78° C.→room temperature for 1 h
  2. customThe reaction mixture is quenched with sat. NH4Cl
  3. extractionextracted with CH2Cl2
  4. dry with materialThe separated CH2Cl2 is dried over Na2SO4
  5. customevaporated

출처 및 근거

ORD 기록
ord-ec880edb7c984eb2b1b57c06290410ff
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557103B2

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