Chlorotrimethylsilane → Ethyl [2-ethyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetate

HRID 1627905Notes

Reaction equation

HRID 1627905 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=O.O=[C:21]([CH2:29][CH3:30])[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].Cl[Si](C)(C)C>CN(C=O)C>[CH2:29]([C:21]1[N:1]=[C:2]2[S:6][C:5]3[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=3[C:3]2=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[C:22]=1[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:30]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 754850(2-amino-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)-(4-methylphenyl)methanoneHCID 12271528Ethyl 4-oxohexanoate

Product 1

HCID 49804857Ethyl [2-ethyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetateYield 64.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(p-tolyl)methanone (0.542 g; 2 mmol) and ethyl 4-oxohexanoate (0.348 g; 2.2 mmol) in dry DMF (8 mL) under a nitrogen atmosphere was added chlorotrimethylsilane (1.02 mL; 8 mmol) dropwise. The mixture was stirred in a sealed tube and heated at 100° C. for 24 h. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and water. The organic phase was successively washed with a saturated solution of sodium hydrogen carbonate, water, brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel column using a gradient of ethyl acetate (1-30%) in heptane to afford 0.508 g (64%) of the title compound as a yellow oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic phase was successively washed with a saturated solution of sodium hydrogen carbonate, water, brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel column

Sources & evidence

ORD record
ord-3cfb31dc4b5441ea9f1df228ce5cf8e7
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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