Water → 5-Bromo-1-(methanesulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 269489ノート

反応式

HRID 269489 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:13][S:14](Cl)(=[O:16])=[O:15].O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:14]([CH3:13])(=[O:16])=[O:15])[C:5]2=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 497588975-Bromo-1-(methanesulfonyl)-1H-pyrrolo[2,3-b]pyridine収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (600 mg, 3.06 mmol) in dry THF (30 mL) was added NaH (246 mg, 6.12 mmol) at room temperature. The suspension was stirred for 30 min before addition of methanesulfonyl chloride (540 mg, 4.80 mmol). The solution was stirred at room temperature for another 30 min and poured into water (50 mL). The aqueous solution was extracted with ethyl acetate (2×30 mL), the combined organic layers were dried over MgSO4 and filtered, the filtrate was evaporated under vacuum to afford white solid (780 mg, 93%). The crude product was used directly for the next reaction. LC/MS: Rt 3.26 mis.; (m/e=275.0, 276.9 (M+H, M+2+H).

後処理

  1. extractionThe aqueous solution was extracted with ethyl acetate (2×30 mL)
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customthe filtrate was evaporated under vacuum

出典と根拠

ORDレコード
ord-b52bd419eb1f4f729888f8c98810de78
出典データセット
uspto-grants-2008_11
特許番号
US07446199B2

反応ノート

読み込み中…