Dichloromethane → 2-[(Bromodifluoromethyl)thio]thiazolo[4,5-b]pyridine

HRID 1279237

반응식

HRID 1279237 반응식
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[SH:10].[H-].[Na+].[Br:13][C:14](Br)([F:16])[F:15].ClCCl>CN(C)C=O>[Br:13][C:14]([F:16])([F:15])[S:10][C:2]1[S:1][C:9]2[C:4]([N:3]=1)=[N:5][CH:6]=[CH:7][CH:8]=2

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 6382DibromodifluoromethaneHCID 24758Sodium hydrideHCID 178527821HCID 178527821, 화합물

생성물 1

HCID 99659872-[(Bromodifluoromethyl)thio]thiazolo[4,5-b]pyridine수율 17.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

A solution of thiazolo[4,5-b]pyridine-2-thiol (2.0 g, 12 mol) in N,N-dimethylformamide is added dropwise to a mixture of sodium hydride (0.96 g, 0.024 mol) in N,N-dimethylformamide over 30 minutes. The resultant reaction mixture is treated with a solution of dibromodifluoromethane (2.52 g) in N,N-dimethylformamide, stirred at room temperature for 24 hours, and poured into an ice-water mixture. The resultant aqueous mixture is extracted with ethyl acetate. The organic extract is washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a residue. Chromatography of the residue using silica gel and dichloromethane followed by azeotropic removal of N,N-dimethylformamide (toluene) affords an oil. The oil is further purified by column chromatography using silica gel and a 20:1 ethyl acetate/hexanes solution to give the title product as a light yellow liquid (0.61 g, 17% yield).

후처리

  1. customThe resultant reaction mixture
  2. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  3. extractionThe organic extract
  4. washis washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue
  8. customfollowed by azeotropic removal of N,N-dimethylformamide (toluene)
  9. customaffords an oil
  10. customThe oil is further purified by column chromatography

출처 및 근거

ORD 기록
ord-ca45060013c34cac83ebd7f6845ec8d4
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448262B1

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