Methyl chloroformate → Methyl 7-chlorothieno[3,2-B]pyridine-2-carboxylate

HRID 500762노트

반응식

HRID 500762 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.[Li]CCCC.Cl[C:17]([O:19][CH3:20])=[O:18]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[S:10][C:3]=12

참가 물질

5

반응물 3

HCID 6586Methyl chloroformateHCID 112752517-Chlorothieno[3,2-b]pyridineHCID 178418339Butyllithium

생성물 1

HCID 59424429Methyl 7-chlorothieno[3,2-B]pyridine-2-carboxylate수율 46%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 2 (7.0 g, 41.3 mmol) in anhydrous THF (100 mL) at −78° C. under a nitrogen atmosphere was added n-BuLi (24.7 mL, 2.5 M in hexanes, 61.8 mmol). After 1 hour, methyl chloroforrnate (9.6 ml, 124 mmol) was added and the reaction mixture was stirred for an extra hour at the same temperature, quenched with excess methanol and allowed to warm to room temperature. The solvent was then evaporated and the residue was purified by flash chromatography using hexane —AcOEt (70:30) as an eluent. The product from the column was re-crystallized from ethyl acetate to afford title compound 37 (4.3g, 46% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.75 (dd, J=0.8 and 4.8 Hz, 1H), 8.26 (d, J=0.8 Hz, 1H), 7.74 (dd, J=0.8 and 5.2 Hz, 1H), 3.93 (s, 3H).

후처리

  1. customquenched with excess methanol
  2. customThe solvent was then evaporated
  3. customthe residue was purified by flash chromatography
  4. customThe product from the column was re-crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-207df06b9c724173a6c5db3cd65710d7
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772247B2

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