Diisopropylethylamine → (S)-Ethyl {N-[(5-bromopyridin-3-yl)carbonyl]-S-phenylsulfonimidoyl}acetate

HRID 1099658

Reaction equation

HRID 1099658 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(N(CC)C(C)C)(C)C.[C:20]1([S:26]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])(=[NH:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:6]([C:7]([N:28]=[S@:26]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:27])=[O:9])[CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 887075-Bromonicotinic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 76585231ethyl(S-phenylsulfonimidoyl)acetate

Product 1

HCID 57657890(S)-Ethyl {N-[(5-bromopyridin-3-yl)carbonyl]-S-phenylsulfonimidoyl}acetateYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromonicotinic acid (343 mg, 1.66 mmol) in anhydrous DMF (5.5 μL) was added N,N-diisopropylethylamine (0.58 mL, 3.32 mmol) and ethyl (S-phenylsulfonimidoyl)acetate (415 mg, 1.83 mmol) followed by the final addition of (benzotriazol-1-yloxy)-tris(dimethylamino)-phosphonium hexafluorophophate (0.81 g, 1.83 mmol). The reaction mixture was stirred at room temperature for 20 min, and then partitioned between saturated aqueous NaHCO3 and EtOAc. The organic layer was separated and washed once with brine and dried over anhydrous Na2SO4. The organic layer was concentrated and the residue purified by chromatography (silica gel, gradient elution (5:1 Hexane/EtOAc to 3:1 Hexane/EtOAc). The product containing fractions were concentrated to give the title compound as a white solid (230 mg, 34%).

Workup

  1. custompartitioned between saturated aqueous NaHCO3 and EtOAc
  2. customThe organic layer was separated
  3. washwashed once with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe organic layer was concentrated
  6. customthe residue purified by chromatography (
  7. washsilica gel, gradient elution (5:1 Hexane/EtOAc to 3:1 Hexane/EtOAc)
  8. additionThe product containing fractions
  9. concentrationwere concentrated

Sources & evidence

ORD record
ord-bed780b4759d4b788659997d4e99fab6
Source dataset
uspto-grants-2012_03
Patent number
US08143410B2

Linked notes

Loading…