Isopropyl iodide → Methyl 6-bromo-3-formyl-1-isopropyl-1H-indazole-4-carboxylate

HRID 85480ノート

反応式

HRID 85480 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[C:5]2[C:6]([CH:11]=[O:12])=[N:7][NH:8][C:9]=2[CH:10]=1.C([O-])([O-])=O.[K+].[K+].I[CH:24]([CH3:26])[CH3:25]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[C:5]2[C:6]([CH:11]=[O:12])=[N:7][N:8]([CH:24]([CH3:26])[CH3:25])[C:9]=2[CH:10]=1

参加物

6

反応物 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 178497028HCID 178497028、化合物

生成物 1

HCID 71742648Methyl 6-bromo-3-formyl-1-isopropyl-1H-indazole-4-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of methyl 6-bromo-3-formyl-1H-indazole-4-carboxylate 1 (11.5 g, 40.63 mmol) in DMF (230 mL)) was added K2CO3 (14.08 g, 102.02 mmol) at RT under argon, and stirred for 10 min. Then 2-iodopropane (7.24 g, 42.58 mmol) was added at RT and the mixture stirred at 40° C. for 2 h. The reaction mixture was diluted with cold water and extracted with ethyl acetate (4×300 mL). The combined organic layers were washed with water, brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude residue (12.4 g) was purified by silica gel chromatography (eluent: 0-10% ethyl acetate: pet ether) to afford the title compound as an off white solid (5.55 g, 42%). 1H NMR (CDCl3, 400 MHz): δ 1.659 (d, J=6.4 Hz, 6H), 4.017 (s, 3H), 4.862-4.960 (m, 1H), 7.807 (s, 1H), 7.854 (s, 1H), 10.375 (s, 1H). HPLC: 98.66%.

後処理

  1. stirringthe mixture stirred at 40° C. for 2 h
  2. extractionextracted with ethyl acetate (4×300 mL)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue (12.4 g) was purified by silica gel chromatography (eluent: 0-10% ethyl acetate: pet ether)

出典と根拠

ORDレコード
ord-bed8b3597309468483d1553451c55f1c
出典データセット
uspto-grants-2014_09
特許番号
US08846935B2

反応ノート

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