Ammonium Chloride → 4-Bromo-7-methyl-6,7-dihydro-5H-cyclopenta[C]pyridin-7-OL

HRID 714051Notes

Reaction equation

HRID 714051 reaction equation
[Br:1][C:2]1[C:3]2[CH2:10][CH2:9][C:8](=[O:11])[C:4]=2[CH:5]=[N:6][CH:7]=1.[CH3:12][Mg]Br.[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[C:3]2[CH2:10][CH2:9][C:8]([CH3:12])([OH:11])[C:4]=2[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 717438924-bromo-5H,6H,7H-cyclopenta[c]pyridin-7-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 898463494-Bromo-7-methyl-6,7-dihydro-5H-cyclopenta[C]pyridin-7-OLYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A brown suspension of 4-bromo-5H-cyclopenta[c]pyridin-7(6H)-one (intermediate A-4[B]) (424 mg, 2.0 mmol) in THF (5 mL) was cooled (−78° C.) and treated during 10 min with methylmagnesium bromide (2.1 mL, 3.0 mmol, 1.4 M in THF:toluene 1:3). The reaction was allowed to warm up to RT over 3 h then stirred for 1.5 h at RT. The mixture was poured on aq. sat. NH4Cl-solution and extracted with EtOAc (3×). The organic layer was dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (4%)) gave the title compound (180 mg, 40%) as dark green viscous oil. MS: 228.0 (M+H+, 1Br).

Workup

  1. temperatureto warm up to RT over 3 h
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (4%))

Sources & evidence

ORD record
ord-b9d7d556353546928620fc65f36ae865
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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