Diisopropylethylamine → (S)-5-bromo-N-[(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)(oxido)phenyl--sulfanylidene]nicotinamide

HRID 607447Notes

Reaction equation

HRID 607447 reaction equation
[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][CH2:7][CH2:8][CH2:9][S@:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[NH:12])=[O:11])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[Br:30][C:31]1([CH:39]=[CH:38][CH:37]=[N:36][CH2:35]1)C(O)=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[C:67]([O-:70])(O)=O.[Na+]>CN(C=O)C>[Br:30][C:31]1[CH:35]=[N:36][CH:37]=[C:38]([CH:39]=1)[C:67]([N:12]=[S@@:10]([CH2:9][CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:2])([CH3:4])[CH3:3])([CH3:20])[CH3:19])(=[O:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:70]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 197679223-Bromonicotinic acidHCID 86629483(S)-tert-butyl(dimethyl)[3-(S-phenylsulfonimidoyl)propoxy]silane

Product 1

HCID 86629482(S)-5-bromo-N-[(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)(oxido)phenyl--sulfanylidene]nicotinamideYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of (S)-tert-butyl(dimethyl)[3-(S-phenylsulfonimidoyl)propoxy]silane (1.55 g, 4.95 mmol) in DMF (15 mL) at room temperature was added N,N-diisopropylethylamine (1.72 mL), 3-bromonicotinic acid (1.07 g), and finally the coupling reagent, (benzotriazol-1-yloxy)-tris(dimethylamino)-phosphonium hexafluorophosphate (2.48 g). The reaction was stirred for 15 min and then poured into saturated aqueous NaHCO3. The aqueous phase was extracted with EtOAC (1×), which was subsequently washed with aqueous NaHCO3, brine (1×), and dried with anhydrous Na2SO4. The organic layer was decanted, concentrated, and the oily residue was subject to a gradient column chromatography (EtOAc-Hex:from 1:20 to 1:6) yielding the title compound as an amber oil (2.39 g, 97%).

Workup

  1. extractionThe aqueous phase was extracted with EtOAC (1×), which
  2. washwas subsequently washed with aqueous NaHCO3, brine (1×)
  3. dry with materialdried with anhydrous Na2SO4
  4. customThe organic layer was decanted
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b8e6880f63cc4427a59c37c3fc19e171
Source dataset
uspto-grants-2011_03
Patent number
US07915443B2

Reaction notes

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