Water → N-(4-Bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide

HRID 2277664Notes

Reaction equation

HRID 2277664 reaction equation
[Br:1][C:2]1[C:3]2[CH2:10][CH2:9][CH:8]([NH2:11])[C:4]=2[CH:5]=[N:6][CH:7]=1.CCN(CC)CC.[C:19](Cl)(=[O:22])[CH2:20][CH3:21].O>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[C:3]2[CH2:10][CH2:9][CH:8]([NH:11][C:19](=[O:22])[CH2:20][CH3:21])[C:4]=2[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 717438934-Bromo-6,7-dihydro-5H-cyclopenta[C]pyridin-7-amine

Product 1

HCID 86685956N-(4-Bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamideYield 37.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-amine (650 mg, 3.05 mmol, 65% purity) and Et3N (400 mg, 3.97 mmol) in THF (20 mL) was added propionyl chloride (219 mg, 2.38 mmol) at 0° C. and stirring continued for 2 hours. Water (10 mL) and EtOAc (10 mL) were added and the aqueous layer was extracted with EtOAc (10 mL×3). The combined organic layers were dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by column chromatography to afford the title compound (200 mg, 37.6%) as a white solid. MS: 270.9 (M+H+, 1Br).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc (10 mL×3)
  2. customThe combined organic layers were dried over anhy
  3. filtrationNa2SO4, filtered
  4. concentrationconcentrated in vacuo
  5. customto give a crude product which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-afb8821ad47948c8ac4d96dcadfb016a
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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