Lithium Chloride → 5-(5-bromo-2-methylpyridin-3-yl)-1-methyl-1H-pyrazolo[4,3-b]pyridine

HRID 879645

반응식

HRID 879645 반응식
Br[C:2]1[C:3]([CH3:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[CH3:10][N:11]1[C:19]2[C:14](=[N:15][C:16]([Sn](CCCC)(CCCC)CCCC)=[CH:17][CH:18]=2)[CH:13]=[N:12]1.[Li+].[Cl-]>O1CCOCC1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:6]1[CH:7]=[C:2]([C:16]2[N:15]=[C:14]3[CH:13]=[N:12][N:11]([CH3:10])[C:19]3=[CH:18][CH:17]=2)[C:3]([CH3:9])=[N:4][CH:5]=1

참가 물질

7

반응물 3

HCID 433294Lithium ChlorideHCID 6197053,5-Dibromo-2-methylpyridineHCID 867001551-methyl-5-(tributylstannyl)-1H-pyrazolo[4,3-b]pyridine

생성물 1

HCID 867004555-(5-bromo-2-methylpyridin-3-yl)-1-methyl-1H-pyrazolo[4,3-b]pyridine

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

To a solution of 3,5-dibromo-2-methylpyridine (320 mg, 1.28 mmol) in dioxane (10 mL), was added 1-methyl-5-(tributylstannyl)-1H-pyrazolo[4,3-b]pyridine (540 mg, 1.28 mmol), CuI (73 mg, 0.38 mmol), LiCl (271 mg, 6.4 mmol) and Pd(PPh3)4 (147 mg, 0.12 mmol). The reaction mixture was heated at 100° C. for 2 h. The reaction was cooled down, washed by sat. NaHCO3, extracted by EtOAc, dried over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-100% EtOAc in hexanes give the product. LCMS-ESI+: calc'd for C13H11BrN4: 303.0 (M+H+); Found: 303.2 (M+H+).

후처리

  1. temperatureThe reaction was cooled down
  2. washwashed by sat. NaHCO3
  3. extractionextracted by EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated down
  7. custompurified by silica gel column
  8. washeluting by 0-100% EtOAc in hexanes
  9. customgive the product

출처 및 근거

ORD 기록
ord-8e01976eaffd47d09812a762b433d697
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

연결된 노트

불러오는 중…