Dichloromethane → 5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

HRID 408159Notes

Reaction equation

HRID 408159 reaction equation
[Cl: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.[OH-].[Na+].C(Cl)Cl>Cl>[Cl: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

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 602052745-chloro-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 581955655-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amineYield 77.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-Chloro-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine (1.20 g, 5.57 mmol) was placed in 6M HCl (30 mL). SnCl2 (5.28 g, 27.8 mmol) was then added, and the reaction was stirred for 30 minutes at room temperature. The reaction was then poured into a mixture of 1M NaOH and ice. The resulting suspension was then raised to a pH of 8 and then extracted with 3:1 DCM:i-PrOH. The combined organic fractions were dried, filtered, and concentrated to give the crude product, which was triturated with 10:1 hexanes:DCM to give the product 5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (0.8 g, 77% yield).

Workup

  1. temperatureThe resulting suspension was then raised to a pH of 8
  2. extractionextracted with 3:1 DCM
  3. customThe combined organic fractions were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas triturated with 10:1 hexanes

Sources & evidence

ORD record
ord-20b5482eb009459ab486c73de3f7c3c4
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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