Dimethylformamide → 1-(4-Fluorobenzyl)-2-(oxazol-2-yl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine

HRID 1814055노트

반응식

HRID 1814055 반응식
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[NH:18][C:9]2=[N:10][CH:11]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:13]=[C:8]2[CH:7]=1.[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1.[H-].[Na+].CN(C)C=O>O>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:18]2[C:9]3=[N:10][CH:11]=[C:12]([S:14]([CH3:17])(=[O:15])=[O:16])[CH:13]=[C:8]3[CH:7]=[C:6]2[C:2]2[O:1][CH:5]=[CH:4][N:3]=2)=[CH:22][CH:21]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 225043982-(oxazol-2-yl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 99293371-(4-Fluorobenzyl)-2-(oxazol-2-yl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine수율 34.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
22.5 °C

실험 절차

A mixture of 2-(oxazol-2-yl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine (0.19 g), 4-fluorobenzyl bromide (0.16 g), sodium hydride (32 mg, 60% purity) and dimethylformamide (10 ml) was stirred at 15 to 30° C. for 30 minutes. To the reaction mixture was added water, and the precipitated crystals were filtered off and dissolved in ethyl acetate. The solution was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue (0.14 g) was recrystallized (ethyl acetate/hexane) to obtain 92 mg of the desired product.

후처리

  1. filtrationthe precipitated crystals were filtered off
  2. dissolutiondissolved in ethyl acetate
  3. dry with materialThe solution was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue (0.14 g) was recrystallized (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-65977eedca9a46799515fbb6947f81f7
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875770B2

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