Potassium sodium tartarate → 7-(4-Fluorophenylsulfonyl)-9-iodo-1,2,4,5-tetrahydro-3-benzazepine

HRID 1784422Notes

Reaction equation

HRID 1784422 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH2:10][C:9]2[C:12]([I:20])=[CH:13][C:14]([S:16](F)(=[O:18])=[O:17])=[CH:15][C:8]=2[CH2:7][CH2:6]1)=O.[F:23][C:24]1[CH:29]=[CH:28][C:27]([Mg]Cl)=[CH:26][CH:25]=1.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCCC1>[F:23][C:24]1[CH:29]=[CH:28][C:27]([S:16]([C:14]2[CH:13]=[C:12]([I:20])[C:9]3[CH2:10][CH2:11][NH:5][CH2:6][CH2:7][C:8]=3[CH:15]=2)(=[O:17])=[O:18])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 866017253-Trifluoroacetyl-9-iodo-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonyl fluorideHCID 178505844HCID 178505844, compound

Product 1

HCID 688303227-(4-Fluorophenylsulfonyl)-9-iodo-1,2,4,5-tetrahydro-3-benzazepineYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-trifluoroacetyl-9-iodo-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonyl fluoride (5.29, 11.5 mmol) in tetrahydrofuran (50 ml) was added 4-fluorophenylmagnesium chloride (50 ml, 1M in tetrahydrofuran, 50 mmol). The resulting solution was stirred for 18 h without cooling then poured into saturated aqueous sodium potassium tartrate (150 ml), and extracted with diethyl ether (100 ml), The resulting organic layer washed with brine (100 ml), dried (MgSO4), and evaporated. Isolation using an SCX column and crystallisation from diethyl ether gave the subtitle compound as a white solid (2.4 g).

Workup

  1. temperaturewithout cooling
  2. extractionextracted with diethyl ether (100 ml)
  3. washThe resulting organic layer washed with brine (100 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customan SCX column and crystallisation from diethyl ether

Sources & evidence

ORD record
ord-53c8c78f7b5a4025936fe3f2f7dc9b60
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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