Sodium Carbonate → 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

HRID 79613

Reaction equation

HRID 79613 reaction equation
[Br:1][C:2]1[C:3]([F:14])=[C:4]2[C:10]([N+:11]([O-])=O)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.Cl[Sn]Cl.C([O-])([O-])=O.[Na+].[Na+]>Cl>[Br:1][C:2]1[C:3]([F:14])=[C:4]2[C:10]([NH2:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24479Stannous ChlorideHCID 602052755-bromo-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amineYield 28.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-bromo-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine (2.0 g, 7.7 mmol) was placed in 6M HCl (30 mL) at room temperature. SnCl2 (7.29 g, 38.5 mmol) was then added, and the reaction was stirred for 30 minutes at room temperature. The reaction was then cooled to 0° C. and a saturated aqueous solution of Na2CO3 was added to raise the pH to 8. The reaction was then extracted with DCM (with minimal MeOH to aid solubility). The combined organic fractions were dried, filtered, and concentrated to give the crude product 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (0.50 g, 28.2% yield), which was used without purification.

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. temperatureto raise the pH to 8
  3. extractionThe reaction was then extracted with DCM (with minimal MeOH to aid solubility)
  4. customThe combined organic fractions were dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-262e553a27c44f969cd6bf6fe0afe17a
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Linked notes

Loading…