Sodium Hydroxide → HCID 59409536, compound

HRID 659951Notes

Reaction equation

HRID 659951 reaction equation
C([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[NH:23][C:22]3[C:17](=[N:18][CH:19]=[C:20]([CH3:24])[CH:21]=3)[C:16]=2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1.[OH-].[Na+]>S(=O)(=O)(O)O>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:16]2[C:17]3=[N:18][CH:19]=[C:20]([CH3:24])[CH:21]=[C:22]3[NH:23][C:15]=2[C:13]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:8])[CH:14]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68429319HCID 68429319, compound

Product 1

HCID 59409536HCID 59409536, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

7.8 g (19 mmoles) of Benzyl-{4-[3-(4-fluoro-phenyl)-6-methyl-1H-pyrrolo[3,2-b]pyridin-2-yl]-pyridin-2-yl}-amine is suspended at room temperature in 40 mL of concentrated sulfuric acid. After 1 hour, the reaction is poured into ice (250 g) and kept at 0° C. while adding 170 mL of concentrated sodium hydroxide solution to reach pH=10. The resulting precipitate is filtered, suspended again in hot water and stirred at reflux for 1 hour. The reaction mixture is then filtered again and washed with hot water to give 6 g of 4-[3-(4-Fluoro-phenyl)-6-methyl-1H-pyrrolo[3,2-b]pyridin-2-yl]-pyridin-2-ylamine as white solid.

Workup

  1. customkept at 0° C.
  2. filtrationThe resulting precipitate is filtered
  3. temperatureat reflux for 1 hour
  4. filtrationThe reaction mixture is then filtered again
  5. washwashed with hot water

Sources & evidence

ORD record
ord-79242fcbb69a493cb71feda462230279
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

Loading…