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

HRID 872029ノート

反応式

HRID 872029 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
110 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-330e90e5ba5c43a2944f43d17faa3171
出典データセット
uspto-grants-2015_03
特許番号
US08975252B2

反応ノート

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