o-Toluenesulfonyl chloride → HCID 49758932、化合物

HRID 1409108ノート

反応式

HRID 1409108 の反応式
[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

参加物

6

反応物 4

HCID 8623o-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydride2 回HCID 468355224-Bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 49758932HCID 49758932、化合物収率 58%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-efdc30931e6f4d3bb80dbc35aa63f81c
出典データセット
uspto-grants-2014_12
特許番号
US08921376B2

反応ノート

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