N-bromobutanimide → 2-Bromo-3,4-dimethyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester

HRID 1019610

Reaction equation

HRID 1019610 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([CH3:13])[C:10]2[C:14]([CH3:17])=[CH:15][S:16][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].C1C(=O)N([Br:25])C(=O)C1>CC(O)=O.C(Cl)(Cl)Cl.CCOC(C)=O>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([CH3:13])[C:10]2[C:14]([CH3:17])=[C:15]([Br:25])[S:16][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 582561263,4-Dimethyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester

Product 1

HCID 669339072-Bromo-3,4-dimethyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl esterYield 75.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21584526Acetic acid chloroformSolvent

Procedure

The product of step (b) (92 mg, 0.36 mmol) was dissolved in 4 mL of 1:1 HOAc/CHCl3 and treated with NBS (67 mg, 0.38 mmol). After stirring for ½ hour, the reaction was diluted with EtOAc (70 mL) was washed with water (3×30 mL) and 1M NaOH (2×30 mL). The organic solution was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (EtOAc/Hex) to give 90 mg of the sub-title compound.

Workup

  1. washwas washed with water (3×30 mL) and 1M NaOH (2×30 mL)
  2. dry with materialThe organic solution was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-3fca66fc30f5411eb234d4d1863ad7fc
Source dataset
uspto-grants-2014_05
Patent number
US08716276B2

Linked notes

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