Water → methyl 1-(3-methoxypropyl)-3-methyl-1H-indazol-6-carboxylate

HRID 872029노트

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HRID 872029 반응식
CB1OB(C)OB(C)O1.[C:10](=O)([O-])[O-].[K+].[K+].Br[C:17]1[C:25]2[C:20](=[CH:21][C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:24]=2)[N:19]([CH2:30][CH2:31][CH2:32][O:33][CH3:34])[N:18]=1.O>O1CCOCC1.Cl[Pd]Cl.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:34][O:33][CH2:32][CH2:31][CH2:30][N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[C:22]([C:26]([O:28][CH3:29])=[O:27])[CH:21]=2)[C:17]([CH3:10])=[N:18]1

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 59494402methyl 3-bromo-1-(3-methoxypropyl)-1H-indazole-6-carboxylate

생성물 1

HCID 59494412methyl 1-(3-methoxypropyl)-3-methyl-1H-indazol-6-carboxylate수율 87.9%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

Trimethylboroxin (513 μL), potassium carbonate (1.27 g) and bis(diphenylphosphino)ferrocene dichloropalladium (224 mg) were added to a solution of methyl 3-bromo-1-(3-methoxypropyl)-1H-indazol-6-carboxylate (1.0 g) in 1,4-dioxane (15 ml) under argon atmosphere and the mixture was stirred at 110° C. for 6 hours. Water was added to the reaction mixture under ice-cooling and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=4/1 to 3/2) to give methyl 1-(3-methoxypropyl)-3-methyl-1H-indazol-6-carboxylate (705 mg) as a yellow powder.

후처리

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=4/1 to 3/2)

출처 및 근거

ORD 기록
ord-330e90e5ba5c43a2944f43d17faa3171
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975252B2

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