Acetic Acid → Ethyl 2-bromo-4,5,7,8-tetrahydro-6H-thieno[2,3-d]azepine-6-carboxylate

HRID 1365610Notes

Reaction equation

HRID 1365610 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[CH:14][S:15][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].CC(O)=O.C1C(=O)N([Br:27])C(=O)C1>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([Br:27])[S:15][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 593025414,5,7,8-Tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester

Product 1

HCID 57354995Ethyl 2-bromo-4,5,7,8-tetrahydro-6H-thieno[2,3-d]azepine-6-carboxylateYield 98.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The product of Example 1, step (d) (80 mg, 0.35 mmol) was dissolved in 2 mL of 1:1 CHCl3:HOAc and treated with NBS (62 mg, 0.35 mmol). After 15 minutes, the reaction was concentrated to dryness, dissolved in a minimal amount of EtOAc and filtered through a pad of silica gel. The filtrate was evaporated to give 105 mg of the sub-title compound.

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. dissolutiondissolved in a minimal amount of EtOAc
  3. filtrationfiltered through a pad of silica gel
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-86162a64c6694d4d9a4beaa034e9ba82
Source dataset
uspto-grants-2011_02
Patent number
US07893051B2

Reaction notes

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