2,3-Dibromo-4-methyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester → 4-Methyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester

HRID 2237445Notes

Reaction equation

HRID 2237445 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([CH3:13])[C:10]2[C:14](Br)=[C:15](Br)[S:16][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([CH3:13])[C:10]2[CH:14]=[CH:15][S:16][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 593025452,3-Dibromo-4-methyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester

Product 1

HCID 593025564-Methyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

The product of step c) (800 mg, 2.0 mmol) was dissolved in 150 mL EtOH and treated with 800 mg of 10% Pd/C (wet, Degussa grade E101). After stirring overnight, another 300 mg of Pd was added and stirring was continued 3 hours. The reaction was filtered through celite, diluted with DCM (300 mL), and washed with water (1×300 mL). The organic layer was dried over MgSO4 and concentrated to give 475 mg of the subtitle compound.

Workup

  1. stirringstirring
  2. waitwas continued 3 hours
  3. filtrationThe reaction was filtered through celite
  4. additiondiluted with DCM (300 mL)
  5. washwashed with water (1×300 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-31214cb11505455f8528cf363fd648da
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

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