Water → 7-[(Pyridin-3-yl)hydroxymethyl]imidazo[5,1-b]thiazole

HRID 1072322노트

반응식

HRID 1072322 반응식
I[C:2]1[N:3]=[CH:4][N:5]2[CH:9]=[CH:8][S:7][C:6]=12.C[Mg]Br.C1COCC1.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]=[O:25])[CH:19]=1.O>C1COCC1>[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([OH:25])[C:2]2[N:3]=[CH:4][N:5]3[CH:9]=[CH:8][S:7][C:6]=23)[CH:19]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 103713-PyridinecarboxaldehydeHCID 177737777-Iodoimidazo[5,1-B]thiazoleHCID 178420675HCID 178420675, 화합물

생성물 1

HCID 223902477-[(Pyridin-3-yl)hydroxymethyl]imidazo[5,1-b]thiazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2.50 g of 7-iodoimidazo[5,1-b]thiazole in 50 ml of dry THF was cooled in ice, and 11.3 ml of a 0.93 M methylmagnesium bromide/THF solution was added to the cooled solution under an argon atmosphere. The mixture was stirred at that temperature for 20 min. Pyridine-3-aldehyde (1.04 ml) was then added thereto, and the mixture was stirred at that temperature for 40 min and then at room temperature for 4 hr. Water was added to the reaction solution, and the mixture was extracted five times with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and was then concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1) to give 1.925 g of 7-[(pyridin-3-yl)hydroxymethyl]imidazo[5,1-b]thiazole.

후처리

  1. stirringthe mixture was stirred at that temperature for 40 min
  2. waitat room temperature for 4 hr
  3. extractionthe mixture was extracted five times with dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationwas then concentrated under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1)

출처 및 근거

ORD 기록
ord-82ca0b1c99f7439c9cca97c0487bd524
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908913B2

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