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Potassium Acetate → 7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-nitroisoquinolin-1(2H)-one

HRID 577598
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HRID 577598 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:12])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1.[CH3:16][N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[N:18]1.CCCCP(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2.C([O-])(=O)C.[K+]>CC(O)(CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:16][N:17]1[C:21]([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][NH:8][C:9]3=[O:12])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=2)=[C:20]([CH3:22])[N:19]=[N:18]1
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참가 물질

7

반응물 4

HCID 517044Potassium AcetateHCID 11371790Bis(adamantan-1-yl)(butyl)phosphaneHCID 152571421,4-Dimethyl-1H-1,2,3-triazoleHCID 825721717-bromo-5-nitroisoquinolin-1(2H)-one

생성물 1

HCID 867238257-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-nitroisoquinolin-1(2H)-one수율 60%

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 64052-Methyl-2-butanol용매

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온도
120 °C

실험 절차

A mixture of 7-bromo-5-nitroisoquinolin-1(2H)-one (293b, 4.00 g, 14.9 mmol), 1,4-dimethyl-1H-1,2,3-triazole (2.17 g, 22.3 mmol), palladium acetate (334 mg, 1.49 mmol), CatacXiumA (butyl di-1-adamantylphosphine) (1.10 g, 2.97 mmol), and potassium acetate (7.30 g, 74.3 mmol) in 2-methyl-2-butanol (100 mL) was degassed with nitrogen, and heated at 120° C. in a sealed tube overnight. After cooling down room temperature, the reaction mixture was partitioned between ethyl acetate (300 mL) and water (300 mL). The organic phase was separated, washed with brine (1×300 mL), dried over sodium sulfate, concentrated to dryness, and purified by silica gel chromatography (eluting with a gradient of 0%-10% methanol in ethyl acetate), affording 7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-nitroisoquinolin-1(2H)-one (293c, 2.55 g, 60% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 11.95 (br. s., 1H), 8.57 (s, 2H), 7.55 (d, J=5.38 Hz, 1H), 6.98 (d, J=7.34 Hz, 1H), 4.00 (s, 3H), 2.29 (s, 3H). MS: 284 [M−1].

후처리

  1. customwas degassed with nitrogen
  2. temperatureAfter cooling down room temperature
  3. customthe reaction mixture was partitioned between ethyl acetate (300 mL) and water (300 mL)
  4. customThe organic phase was separated
  5. washwashed with brine (1×300 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness
  8. custompurified by silica gel chromatography (
  9. washeluting with a gradient of 0%-10% methanol in ethyl acetate),

출처 및 근거

ORD 기록
ord-4af0cc07c1024da7ace15f6b0501fcb9
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09040515B2

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