Dimethylformamide → 1H-Indazole-5-carboxaldehyde

HRID 240753

반응식

HRID 240753 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.C([Li])CCC.CN(C)[CH:18]=[O:19]>O1CCCC1>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([CH:18]=[O:19])=[CH:10][CH:9]=2)[CH:5]=[N:6]1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 7619295-bromo-1H-indazoleHCID 178418339Butyllithium

생성물 1

HCID 212506441H-Indazole-5-carboxaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-bromoindazole (5 g, 25.38 mmol) in tetrahydrofuran (100 mL) cooled at −50° C. under argon was added dropwise a solution of 1.6 M n-butyllithium in hexanes (40 mL, 63.44 mmol). Dimethylformamide (3.9 mL, 50.75 mmol) was added, and the mixture was allowed to warm to room temperature and stirred for 15 minutes. The mixture was then quenched with water, extracted with ethyl acetate, preabsorbed onto silica gel and purified by silica gel chromatography eluting with a gradient of 10-30% ethyl acetate in hexanes to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 10.03 (s, 1H) 8.45 (s, 1H) 8.35 (s, 1H) 7.85 (dd, J=8.70, 1.37 Hz, 1H) 7.69 (d, J=8.54 Hz, 1H).

후처리

  1. customThe mixture was then quenched with water
  2. extractionextracted with ethyl acetate
  3. custompreabsorbed onto silica gel
  4. custompurified by silica gel chromatography
  5. washeluting with a gradient of 10-30% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-231ed7d086304deb8df884dcab593ff5
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648069B2

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