Acetonitrile → HCID 178505545, compound

HRID 42582Notes

Reaction equation

HRID 42582 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:11]=[C:10]3[NH:27][N:28]=[CH:29][C:9]=23)=[CH:4][CH:3]=1.[Br:30]Br.C(#N)C>C(Cl)(Cl)Cl>[Br:30][C:29]1[C:9]2[C:10](=[N:11][C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[C:13]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)[C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[NH:27][N:28]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24408BromineHCID 119613744,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 178505545HCID 178505545, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a suspension of 4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (1.00 g, 2.6 mmol, obtained in example 1) in CHCl3 (10 mL), a solution of Br2 (0.69 g, 4.3 mmol) in CHCl3 (3 mL) was added under argon atmosphere. Acetonitrile (4 mL) was added and the mixture was stirred at room temperature for 2 days. The residue was concentrated, dissolved in CHCl3 and washed with 1 N NaOH. A precipitate was formed, which was filtered and dissolved with MeOH. The solution was concentrated and washed with 1 N NaOH. It was extracted with EtOAc, dried over Na2SO4 and concentrated. This was treated with diethyl ether, the solvent was decanted and the product obtained was dried to afford 1.16 g of the title compound (yield: 97%).

Workup

  1. concentrationThe residue was concentrated
  2. dissolutiondissolved in CHCl3
  3. washwashed with 1 N NaOH
  4. customA precipitate was formed
  5. filtrationwhich was filtered
  6. dissolutiondissolved with MeOH
  7. concentrationThe solution was concentrated
  8. washwashed with 1 N NaOH
  9. extractionIt was extracted with EtOAc
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated
  12. additionThis was treated with diethyl ether
  13. customthe solvent was decanted
  14. customthe product obtained
  15. customwas dried

Sources & evidence

ORD record
ord-6c1edb1c28bc4b1497ccbb7d77703eb0
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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