Sodium Carbonate → HCID 68428588, compound

HRID 659943Notes

Reaction equation

HRID 659943 reaction equation
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[NH:4][C:3]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:23]1([CH3:32])[CH:28]=[CH:27][CH:26]=[C:25](B(O)O)[CH:24]=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1.C(O)C>[N:14]1[CH:15]=[CH:16][C:11]([C:3]2[NH:4][C:5]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[C:2]=2[C:25]2[CH:24]=[C:23]([CH3:32])[CH:28]=[CH:27][CH:26]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 27339503-Tolylboronic acidHCID 68430523HCID 68430523, compound

Product 1

HCID 68428588HCID 68428588, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of 274 mg (1 mmole) of 3-Bromo-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridine in 1.8 mL of toluene under nitrogen is added a 0.6 mL of a 2N solution of sodium carbonate, 170 mg (1.25 mmole) of m-tolylboronic acid and 1.2 mL of ethanol. To the reaction mixture is finally added 45 mg of tetrakistriphenylphosphine palladium. The reaction mixture is sealed in a microwave vessel and stirred under microwave conditions at 180° C. for 2 min. The cooled reaction mixture is then poured into ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulfate. The solid residue after concentration is recrystallized into hexane to afford 150 mg of 2-Pyridin-4-yl-3-m-tolyl-1H-pyrrolo[3,2-b]pyridine as white crystals.

Workup

  1. customThe reaction mixture is sealed in a microwave vessel
  2. customThe cooled reaction mixture
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solid residue after concentration
  7. customis recrystallized into hexane

Sources & evidence

ORD record
ord-e79e016f86244967a113f59fa959a156
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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