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2,2'-Bipyridine → 2-Trifluoromethyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester

HRID 2237449
Notes
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Reaction equation

HRID 2237449 reaction equation
C(O[C:4](=O)[CH2:5][N:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:7][CH2:8][C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)C.N1C=CC=CC=1C1C=CC=CN=1.[F-].[K+].C[Si]([C:38]([F:41])([F:40])[F:39])(C)C>CN(C=O)C.[Cu]I.CN1C(=O)CCC1>[CH2:17]([O:16][C:14]([N:6]1[CH2:5][CH2:4][C:13]2[CH:12]=[C:11]([C:38]([F:41])([F:40])[F:39])[S:10][C:9]=2[CH2:8][CH2:7]1)=[O:15])[CH3:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 14742,2'-BipyridineHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 66934051[Ethoxycarbonyl-(2-thiophen-2-yl-ethyl)-amino]acetic acid ethyl ester

Product 1

HCID 684758472-Trifluoromethyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 6228DimethylformamideSolvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of the product from step a.) (75 mg, 0.21 mmol) in DMF (0.5 ml) and NMP (0.5 ml) was treated with bipyridyl (43 mg, 0.27 mmol), CuI (44 mg, 0.23 mmol), KF (13 mg, 0.23 mmol) and trimethylsilyltrifluoromethane (2.1 ml, 1.05 mmol). The reaction mixture was heated to 80° C. for 3 days. The reaction was cooled and filtered through celite washing with EtOAc (20 ml). The eluent was washed with brine (2×3 ml) and dried (MgSO4) providing the subtitle compound as a brown oil that was used without further purification.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. washthrough celite washing with EtOAc (20 ml)
  4. washThe eluent was washed with brine (2×3 ml)
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-2bdb7c26d0cb4058bb29788725dfe7de
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07718647B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes