Dimethylformamide → 1H-Indazole-5-carboxaldehyde

HRID 240753

反応式

HRID 240753 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 212506441H-Indazole-5-carboxaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-231ed7d086304deb8df884dcab593ff5
出典データセット
uspto-grants-2014_02
特許番号
US08648069B2

関連ノート

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