Sodium Carbonate → 5-(1-Methyl-1H-pyrazol-4-YL)-1H-pyrrolo[2,3-B]pyridine

HRID 1035476Notes

Reaction equation

HRID 1035476 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][N:12]1[CH:16]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:14]=[N:13]1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.[Pd]>[CH3:11][N:12]1[CH:16]=[C:15]([C:2]2[CH:3]=[C:4]3[CH:5]=[CH:6][NH:7][C:8]3=[N:9][CH:10]=2)[CH:14]=[N:13]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 580861115-(1-Methyl-1H-pyrazol-4-YL)-1H-pyrrolo[2,3-B]pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

8.1 A suspension of 1.00 g (5.0 mmol) of 5-bromo-7-azaindole, 2.00 g (9.1 mmol) of 1-methylpyrazole-4-boronic acid pinacol ester, 300 mg (0.26 mmol) of Pd[(PPh3]4 and 9 ml of Na2CO3 (addition as 2 M solution) in 12 ml of DMF is heated at 120° C. under microwave conditions for 30 min. The reaction mixture is filtered, and the filtrate is evaporated. The residue is purified on a silica-gel column with dichloromethane/methanol as eluent, giving 5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine as yellow solid, ESI 199

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated
  3. customThe residue is purified on a silica-gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-82aa53eaa5fc49e6b78df0775ee79ab0
Source dataset
uspto-grants-2013_10
Patent number
US08546390B2

Reaction notes

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