HCID 68427420, compound → HCID 59409518, compound

HRID 659960Notes

Reaction equation

HRID 659960 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[NH:10][C:9]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19](SC)[N:18]=2)=[CH:4][CH:3]=1>C(O)C.N.[Ni]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[NH:10][C:9]=2[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][N:18]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 68427420HCID 68427420, compound

Product 1

HCID 59409518HCID 59409518, compoundYield 51.9%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

560 mg (1.66 mmoles) of 3-(4-Fluoro-phenyl)-2-(2-methylthio-pyrimidin-4-yl)-1H-pyrrolo[3,2-b]pyridine is stirred at room temperature in a mixture of 50 mL of absolute ethanol and 40 mL of ammonia (15% in water). 2 g of Raney nickel (50% in water) is then added to the solution which is further stirred for 3 hours under refluxing conditions. Once cooled, the reaction mixture is filtered over celite and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulfate. The solid residue after concentration is solubilised in ethyl acetate and purified by chromatography on silica gel (ethylacetate/hexane 1/1) to give 250 mg of 3-(4-Fluoro-phenyl)-2-pyrimidin-4-yl-1H-pyrrolo[3,2-b]pyridine as yellowish solid.

Workup

  1. temperatureOnce cooled
  2. filtrationthe reaction mixture is filtered over celite
  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. custompurified by chromatography on silica gel (ethylacetate/hexane 1/1)

Sources & evidence

ORD record
ord-5d32ac332e6b4ebf95a47e22f6ead307
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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