Trimethylsilyl iodide → 4H,5H,6H,7H,8H-thieno[2,3-d]azepine

HRID 2237429Notes

Reaction equation

HRID 2237429 reaction equation
C(OC([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)C.[Si](I)(C)(C)C>C(Cl)(Cl)Cl>[S:15]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:12][CH2:11][C:10]=2[CH:13]=[CH:14]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 593025414,5,7,8-Tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester

Product 1

HCID 115137774H,5H,6H,7H,8H-thieno[2,3-d]azepine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

The product of step d) (200 mg, 0.89 mmol) was dissolved in 15 mL CHCl3 and treated with TMSI (4.5 mmol, 600 uL). After heating to 70° C. overnight, the reaction was carefully quenched with MeOH (10 mL) and 1 M NaOH (20 mL). The subtitle compound was extracted into DCM (3×20 mL). The extracts were dried over MgSO4 and concentrated to give 178 mg of the subtitle compound. 1H NMR (300 MHz, DMSO) 7.20 (d, J=5 Hz, 1H), 6.85 (d, J=5 Hz, 1H), 3.42-3.61 (m, 4H), 2.71-3.03 (m, 4H). MS: ESI (positive): 154 (M+H).

Workup

  1. customthe reaction was carefully quenched with MeOH (10 mL) and 1 M NaOH (20 mL)
  2. extractionThe subtitle compound was extracted into DCM (3×20 mL)
  3. dry with materialThe extracts were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-743839f277c94793b4a6a69745f4fa5a
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

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