Sodium Bicarbonate → Methyl 1-isopropyl-6-(1H-pyrazol-4-yl)-1H-indazole-4-carboxylate

HRID 85445

反応式

HRID 85445 の反応式
Br[C:2]1[CH:3]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[N:28][NH:29][CH:30]=2)O1.C([O-])(O)=O.[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH:11]([N:8]1[C:9]2[CH:10]=[C:2]([C:26]3[CH:27]=[N:28][NH:29][CH:30]=3)[CH:3]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[C:5]=2[CH:6]=[N:7]1)([CH3:13])[CH3:12]

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 67464993Methyl 6-bromo-1-isopropyl-1H-indazole-4-carboxylate

生成物 1

HCID 67467921Methyl 1-isopropyl-6-(1H-pyrazol-4-yl)-1H-indazole-4-carboxylate

試薬・触媒・溶媒 3

HCID 178418807HCID 178418807、化合物触媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of methyl 6-bromo-1-isopropyl-1H-indazole-4-carboxylate, 1 (0.8 g, 2.7 mmol) in 1,4-dioxane (20 mL) were added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.576 g, 2.97 mmol) and NaHCO3 (0.567 g, 6.75 mmol) dissolved in water (8 mL). The reaction mixture was degassed with argon gas for 30 min. To the resulting mixture was added PdCl2(dppf)-CH2Cl2 adduct (0.110 g, 0.135 mmol) and the mixture heated at reflux for 3 h. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (100 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to afford 800 mg of crude product. The crude compound was purified by silica gel chromatography (eluent: 5% MeOH/DCM) to the title compound as a pale liquid (375 mg, 47%). LCMS (ES−) m/z=283.11.

後処理

  1. customThe reaction mixture was degassed with argon gas for 30 min
  2. temperaturethe mixture heated
  3. temperatureat reflux for 3 h
  4. extractionextracted with ethyl acetate (100 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-3193044db6a743a7a19b159b320942a3
出典データセット
uspto-grants-2014_09
特許番号
US08846935B2

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