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

HRID 879645

反応式

HRID 879645 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-8e01976eaffd47d09812a762b433d697
出典データセット
uspto-grants-2015_03
特許番号
US08987250B2

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