o-Toluenesulfonyl chloride → HCID 49758932, 화합물

HRID 1409108노트

반응식

HRID 1409108 반응식
[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.[H-].[Na+].[C:14]1(C)[C:15]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1.[CH3:25]COC(C)=O>CN(C=O)C>[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]2[N:9]([S:20]([C:15]3[CH:14]=[CH:19][C:18]([CH3:25])=[CH:17][CH:16]=3)(=[O:21])=[O:22])[CH:10]=[CH:11][C:3]=12

참가 물질

6

반응물 4

HCID 8623o-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydride2회HCID 468355224-Bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 49758932HCID 49758932, 화합물수율 58%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine (D) (1.89 g, 8.16 mmol) in DMF (15 mL) at 0° C. was added NaH (60% in oil, 328 mg) followed by toluenesulfonylchloride (1.72 g, 8.98 mmol). The reaction mixture was warmed to RT and additional NaH (60% in oil, 2×200 mg) was added at 1 h intervals. After a further 1 h, EtOAc was added and the reaction was quenched with sat'd NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (SiO2, 7% EtOAc in hexanes) provided 4-bromo-5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine (E) (1.81 g, 58%) as an off white solid. LC/MS Tret=4.8 min, (M+H+) 386.6.

후처리

  1. customthe reaction was quenched with sat'd NaHCO3
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-efdc30931e6f4d3bb80dbc35aa63f81c
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921376B2

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