Sulfuric Acid → 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

HRID 245782노트

반응식

HRID 245782 반응식
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([CH2:11][OH:12])=[CH:9][N:8](CO)[C:5]2=[N:6][CH:7]=1.[OH:15]S(O)(=O)=O>CC(C)=O.O>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([C:11]([OH:12])=[O:15])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

참가 물질

5

반응물 2

HCID 1118Sulfuric AcidHCID 57516585(2-Bromo-5H-pyrrolo[2,3-b]pyrazine-5,7-diyl)dimethanol

생성물 1

HCID 866778972-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid수율 107.3%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

To a stirred solution of (2-bromo-7-hydroxymethyl-pyrrolo[2,3-b]pyrazin-5-yl)-methanol (0.525 g, 2.03 mmol) in 200 mL of acetone at 40° C. was added a solution of CrO3 (0.832 g, 8.32 mmol) and H2SO4 (1.32 g, 13.4 mmol) in water (3 ml). Then the reaction was stirred at 40° C. for 16 hours then filtered through Celite. The filtrate was evaporated at 40° C. under reduced pressure to give 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.527 g) as an off-white solid. LCMS: (M+H)+=264; 1H NMR (300 MHz, DMSO-d6): δ 13.04 (s, 1H), 8.53 (s, 1H), 8.45 (s, 1H), 5.63 (s, 1H).

후처리

  1. filtrationthen filtered through Celite
  2. customThe filtrate was evaporated at 40° C. under reduced pressure

출처 및 근거

ORD 기록
ord-97f27a06f8eb4868af5ee4aae03799e6
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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