Water → HCID 68427420, compound

HRID 659959Notes

Reaction equation

HRID 659959 reaction equation
Cl[C:2]1[C:7]([N:8]=[C:9]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([S:24][CH3:25])[N:19]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:6][CH:5]=[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]=[CH:5][CH:6]=[C:7]3[NH:8][C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[C:20]([S:24][CH3:25])[N:19]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 962WaterHCID 9237DabcoHCID 86643500HCID 86643500, compound

Product 1

HCID 68427420HCID 68427420, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

6.5 g (14.7 mmoles) of (2-Chloro-pyridin-3-yl)-[2-(4-fluoro-phenyl)-1-(2-methylthio-pyrimidin-4-yl)-ethylidene]-amine is dissolved in 60 mL of dimethylformamide under nitrogen. 6.2 g of DABCO (52 mmoles) and 0.5 g of bis(triphenylphosphine)palladium dichloride are subsequently added to the reaction mixture which is stirred for 4 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 in diethyl ether to afford 4 g of 3-(4-Fluoro-phenyl)-2-(2-methylthio-pyrimidin-4-yl)-1H-pyrrolo[3,2-b]pyridine as a yellowish solid.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solid residue after concentration
  6. customis recrystallized in diethyl ether

Sources & evidence

ORD record
ord-855881ce32074e8781e9d5d92cf26483
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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