Water → 3-(4-Fluoro-phenyl)-6-methyl-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridine

HRID 659936Notes

Reaction equation

Cl[C:2]1[C:7]([N:8]=[C:9]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:6][C:5]([CH3:24])=[CH:4][N:3]=1.C1N2CCN(CC2)C1.O>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:2]3=[N:3][CH:4]=[C:5]([CH3:24])[CH:6]=[C:7]3[NH:8][C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 120 °C

Procedure

6.15 g (18.1 mmoles) of (2-Chloro-5-methyl-pyridin-3-yl)-[2-(4-fluoro-phenyl)-1-pyridin-4-yl-ethylidene]-amine are dissolved in 100 mL of dimethylformamide under nitrogen. 6.4 g of DABCO (56 mmoles) and 610 mg of bis(triphenylphosphine)palladium dichloride are subsequently added to the reaction mixture which is stirred for 5 hours at 120° C. The cooled reaction mixture is then poured into water 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 ethyl acetate to afford 5.3 g of 3-(4-Fluoro-phenyl)-6-methyl-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridine as a yellowish solid.

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 ethyl acetate

Sources & evidence

ORD record: ord-41e2392d557742a881815db385dda39f
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084395B2

Reaction notes

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