Ammonium Acetate → 4-Bromo-6,7-dihydro-5H-cyclopenta[C]pyridin-7-amine

HRID 2277663Notes

Reaction equation

HRID 2277663 reaction equation
CC([O-])=O.[NH4+].[BH3-][C:7]#[N:8].[Na+].[Br:10][C:11]1[C:12]2[CH2:19][CH2:18]C(=O)[C:13]=2[CH:14]=[N:15][CH:16]=1>CCO>[Br:10][C:11]1[C:12]2[CH2:19][CH2:18][CH:7]([NH2:8])[C:13]=2[CH:14]=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 717438924-bromo-5H,6H,7H-cyclopenta[c]pyridin-7-one

Product 1

HCID 717438934-Bromo-6,7-dihydro-5H-cyclopenta[C]pyridin-7-amineYield 90.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

CH3COONH4 (4.8 g, 62 mmol), NaCNBH3 (315 mg, 5 mmol) and 4-bromo-5H-cyclopenta[c]pyridin-7(6H)-one (1.0 g, 4.15 mmol) in EtOH (10 mL) was added to a sealed microwave vial. The mixture was subject to microwave radiation at 130° C. for 4 min. After the majority of EtOH was evaporated under reduced pressure, it was treated with aq. 2 N NaOH until pH>10 and extracted with EtOAc (50 mL x2). The combined organic layers were dried over anhy. Na2SO4, filtered, and concentrated under reduced pressure to give a crude title product (800 mg) which was used in the next step reaction without further purification. MS: 212.9 (M+H+, 1Br).

Workup

  1. customAfter the majority of EtOH was evaporated under reduced pressure, it
  2. additionwas treated with aq. 2 N NaOH until pH>10
  3. extractionextracted with EtOAc (50 mL x2)
  4. customThe combined organic layers were dried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d2676f1521d44b1a4bc8c7cc80063f5
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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