Methyl iodide → 2-[methyl-N-(methoxycarbonyl)amino]-6-(phenylthio)imidazo[1,2-a]pyridine

HRID 1732479노트

반응식

HRID 1732479 반응식
[CH3:1][O:2][C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[CH:21]=1)=[O:4].O1CCC[CH2:23]1.C([Li])CCC.CI>CCCCCC>[CH3:23][N:5]([C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:10][N:9]2[CH:21]=1)[C:3]([O:2][CH3:1])=[O:4]

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 12414300Methyl [6-(phenylsulfanyl)imidazo[1,2-a]pyridin-2-yl]carbamateHCID 178418339Butyllithium

생성물 1

HCID 540494562-[methyl-N-(methoxycarbonyl)amino]-6-(phenylthio)imidazo[1,2-a]pyridine

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

A suspension of 1.0 g. (0.0033 moles) of 2-(methoxycarbonylamino)-6-(phenylthio)imidazo [1,2-a] pyridine in 35 ml. of tetrahydrofuran under a argon atmosphere is treated dropwise with 1.35 ml. of a 2.45 molar solution of butyllithium in hexane at -20° C. The resultant solution is stirred for 5 minutes and 0.469 g. (0.0033 moles) of methyliodide is added. The reaction mixture is allowed to warm to room temperature and stirred for 30 minutes. The solution is diluted with ice water and the solids are collected by filtration, washed with water and dried. The solid materials is chromatographed on silica gel and eluted with 1:99 methanol in methylene chloride affording 2-[methyl-N-(methoxycarbonyl)amino]-6-(phenylthio)imidazo [1,2-a] pyridine m.p. 147°-149° C.

후처리

  1. additionA suspension of 1.0 g
  2. customat -20° C
  3. filtrationthe solids are collected by filtration
  4. washwashed with water
  5. customdried
  6. customThe solid materials is chromatographed on silica gel
  7. washeluted with 1:99 methanol in methylene chloride

출처 및 근거

ORD 기록
ord-4d21daa091744738bb448cc666717126
출처 데이터셋
uspto-grants-1980_12
특허 번호
US04237300

반응 노트

불러오는 중…