Bromocyclopentane → HCID 66597185, compound

HRID 1627799Notes

Reaction equation

HRID 1627799 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:3]=1[CH2:21][C:22]([O:24][CH3:25])=[O:23].[H-].[Na+].Br[CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.[Cl-].[NH4+]>CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:3]=1[CH:21]([CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 4

HCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 66597278HCID 66597278, compound

Product 1

HCID 66597185HCID 66597185, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according the following procedure: To a solution of methyl [2-Methyl-4-(4-methylphenyl)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl]acetate in dry DMF (4 mL) at −10° C. was added sodium hydride (60% in mineral oil) (0.048 g; 1.2 mmol) and bromocyclopentane (0.120 mL; 1.5 mmol). The reaction mixture was allowed to warm up to room temperature and stirred for 18 h. The reaction mixture was then heated to 70° C. for 24 h. A saturated solution of ammonium chloride (10 ml) was added and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over magnesium sulphatesulphate and concentrated under reduced pressure. The crude material was purified by flash-chromatography on silica gel column using a gradient of ethyl acetate (3 to 30%) in heptane to furnish 0.077 g (18%) of the title compound as a colorless oil.

Workup

  1. customThis compound was prepared
  2. temperatureThe reaction mixture was then heated to 70° C. for 24 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphatesulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash-chromatography on silica gel column

Sources & evidence

ORD record
ord-04b921fdaca54c7ea141c5687e2d45de
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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