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

HRID 879645

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

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+).

Workup

temperatureThe reaction was cooled down
washwashed by sat. NaHCO3
extractionextracted by EtOAc
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated down
custompurified by silica gel column
washeluting by 0-100% EtOAc in hexanes
customgive the product

Sources & evidence

ORD record: ord-8e01976eaffd47d09812a762b433d697
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Linked notes

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