Sodium Carbonate → 1-Methyl-2-pyridin-4-yl-3-(3-trifluoromethyl-phenyl)-1H-pyrrolo[3,2-b]pyridine

HRID 659940Notes

Reaction equation

I[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]([CH3:11])[C:3]=1[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:24][C:25]([F:36])([F:35])[C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1.C(O)C>[CH3:11][N:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:2]([C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([C:25]([F:36])([F:35])[F:24])[CH:31]=2)=[C:3]1[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 130 mg (0.39 mmoles) of 3-Iodo-1-methyl-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridine in 5 mL of toluene under nitrogen is added a 1 mL of a 2N solution of sodium carbonate, 78 mg (0.4 mmole) of 3-trifluoromethyl phenylboronic acid and 1 mL of ethanol. To the reaction mixture is finally added 24 mg of tetrakistriphenylphosphine palladium before heating at 80° C. for 10 hours. 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 70 mg of 1-Methyl-2-pyridin-4-yl-3-(3-trifluoromethyl-phenyl)-1H-pyrrolo[3,2-b]pyridine as white crystals.

Workup

customThe cooled reaction mixture
extractionextracted with ethyl acetate
washThe organic phase is washed with water
dry with materialdried over magnesium sulfate
concentrationThe solid residue after concentration
customis recrystallized into hexane

Sources & evidence

ORD record: ord-bf4a5b477d8646ac92237dfdca00b65e
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084395B2

Reaction notes

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