Sodium Carbonate → tert-butyl 2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)ethylcarbamate

HRID 1360475

반응식

HRID 1360475 반응식
Br[C:2]1[C:3]([C:20]#[N:21])=[N:4][N:5]([CH2:17][CH2:18][CH3:19])[C:6]=1[CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].Cl.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)CC>[NH2:21][C:20]1[C:3]2=[N:4][N:5]([CH2:17][CH2:18][CH3:19])[C:6]([CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[C:2]2[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=1

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 164270902-Aminophenylboronic acid hydrochlorideHCID 66958960tert-butyl 2-(4-bromo-3-cyano-1-propyl-1H-pyrazol-5-yl)ethylcarbamate

생성물 1

HCID 66958848tert-butyl 2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)ethylcarbamate수율 44.7%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매2회HCID 10311-Propanol용매

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온도
100 °C

실험 절차

A flask containing a mixture of tert-butyl 2-(4-bromo-3-cyano-1-propyl-1H-pyrazol-5-yl)ethylcarbamate (15.8 g, 44.2 mmol), 2-aminophenylboronic acid hydrochloride (11.5 g, 66.3 mmol), triphenylphosphine (1.04 g, 3.98 mmol), palladium (II) acetate (299 mg, 1.33 mmol), 2 M aqueous sodium carbonate (67 mL, 133 mmol), 1-propanol (77.4 mL), and water (15.5 mL) was heated overnight under a nitrogen atmosphere in a 100° C. oil bath. The reaction was allowed to cool to ambient temperature and water (300 mL) was added. The mixture was extracted with chloroform, dried over magnesium sulfate, filtered, and concentrated to provide an oil that was purified twice by flash chromatography (silica gel, first column: eluted sequentially with 0-10% CMA in chloroform, and then 25% CMA in chloroform; second column: gradient elution with 50-60% ethyl acetate in hexanes) to yield 7.3 g of tert-butyl 2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)ethylcarbamate as a yellow resin.

후처리

  1. additionA flask containing
  2. temperatureto cool to ambient temperature
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide an oil that
  8. customwas purified twice by flash chromatography (silica gel, first column
  9. washeluted sequentially with 0-10% CMA in chloroform
  10. washsecond column: gradient elution with 50-60% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-55c1a403d6274c1bb32e1309d1eaa703
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879849B2

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