Sodium Carbonate → 1,2-dimethyl-2H-pyrazolo[3,4-c]quinolin-4-amine

HRID 1360440

반응식

HRID 1360440 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.Br[C:32]1[C:33]([C:39]#[N:40])=[N:34][N:35]([CH3:38])[C:36]=1[CH3:37].C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.ClCCl.C(O)CC>[CH3:37][C:36]1[N:35]([CH3:38])[N:34]=[C:33]2[C:32]=1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[N:21]=[C:39]2[NH2:40]

참가 물질

9

반응물 4

HCID 10340Sodium Carbonate2회HCID 11776TriphenylphosphineHCID 164270902-Aminophenylboronic acid hydrochloride2회HCID 669589664-bromo-1,5-dimethyl-1H-pyrazole-3-carbonitrile

생성물 1

HCID 577175181,2-dimethyl-2H-pyrazolo[3,4-c]quinolin-4-amine수율 20%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매2회HCID 962Water용매3회HCID 10311-Propanol용매HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

Triphenylphosphine (0.10 g, 0.45 mmol), 2-aminophenylboronic acid hydrochloride (3.89 g, 22.0 mmol), and 4-bromo-1,5-dimethyl-1H-pyrazole-3-carbonitrile (prepared as described in Parts A-C of Example 5, 3.00 g, 15.0 mmol) were placed in a flask. After 1-propanol was added (22 mL), the flask was placed under vacuum and back-filled with nitrogen three times. Palladium (II) acetate (30 mg, 0.15 mmol) was added, followed by aqueous sodium carbonate (22.5 mL of 2 M) and water (4.4 mL). The reaction was heated overnight under a nitrogen atmosphere at 100° C. Additional 2-aminophenylboronic acid hydrochloride (1.0 g), palladium (II) acetate (approximately 10 mg), aqueous sodium carbonate (10 mL of 2 M), and water (5 mL) were added. The reaction was heated at 100° C. for 8 hours, then was allowed to cool to ambient temperature. The reaction mixture was partioned between dichloromethane and water. The organic layer was concentrated under reduced pressure and the crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-30% CMA in chloroform). The appropriate fractions were combined and concentrated under reduced pressure. The residue was dissolved in dichloromethane and concentrated under reduced pressure, which resulted in the formation of a solid. Hexanes were added to the solid, which was isolated by filtration and crystallized from acetonitrile to yield 0.637 g of 1,2-dimethyl-2H-pyrazolo[3,4-c]quinolin-4-amine as white needles, mp>250° C.

후처리

  1. additionback-filled with nitrogen three times
  2. temperatureThe reaction was heated at 100° C. for 8 hours
  3. temperatureto cool to ambient temperature
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-30% CMA in chloroform)
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in dichloromethane
  8. concentrationconcentrated under reduced pressure, which
  9. customresulted in the formation of a solid
  10. customwhich was isolated by filtration
  11. customcrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-3c29e927913b46a68c051655143cef0c
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879849B2

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