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

HRID 85480노트

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HRID 85480 반응식
[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

참가 물질

6

반응물 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 178497028HCID 178497028, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-bed8b3597309468483d1553451c55f1c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846935B2

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