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

HRID 1476410

반응식

HRID 1476410 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418807HCID 178418807, 화합물촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-59d4437b9537419db01ea2e1b794eb59
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018382B2

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