Potassium Iodide → HCID 49805719, compound

HRID 1627808Notes

Reaction equation

HRID 1627808 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].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.[CH2:41](Br)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.[I-].[K+].[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]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:22]([O:24][CH3:25])=[O:23]

Participants

8

Reactant 6

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 66597278HCID 66597278, compound

Product 1

HCID 49805719HCID 49805719, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 (0.175 g; 0.5 mmol) in dry DMF (2 mL) at −10° C. was added LHMDS 1N in THF (0.55 mL; 0.55 mmol), benzylbromide (0.122 mL; 1 mmol) and potassium iodide (0.166 g; 1 mmol). The reaction mixture was allowed to warm up to room temperature and stirred for 19 h. A saturated solution of ammonium chloride (4 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 using a gradient of ethyl acetate (5 to 40%) in heptane to furnish 0.159 g (72%) of the title compound as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over magnesium sulphatesulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by flash-chromatography on silica gel using a gradient of ethyl acetate (5 to 40%) in heptane

Sources & evidence

ORD record
ord-dd18dc32d6914bf69841295dba4aff51
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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