Sodium Bicarbonate → HCID 23521677, compound

HRID 392435Notes

Reaction equation

HRID 392435 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]([C:19]1[CH:20]=[C:21]([N:25]([CH2:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])[CH:22]=[CH:23][CH:24]=1)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:38]([O-])(O)=O.[Na+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:12]1([C:11]([C:19]2[CH:20]=[C:21]([N:25]([CH2:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)[S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])[CH:22]=[CH:23][CH:24]=2)=[CH2:38])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 23521689HCID 23521689, compound

Product 1

HCID 23521677HCID 23521677, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of methyltriphenylphosphonium bromide (0.269 g, 0.752) in 3 mL THF at 0° C. was added KHMDS (0.5 M in toluene, 1.5 mL, 0.752 mmol). The mixture was warmed to ambient temperature for 1 h and N-(3-benzoylphenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine (0.143 g, 0.376 mmol) as a solution in 3 mL THF was added via cannula. After 3 h the mixture was poured into saturated NaHCO3 solution and Extracted with EtOAc, dried over MgSO4, filtered and concentrated. The residue was chromatographed with 10:1 to 5:1 DCM/EtOAc to give the title compound as a clear oil. 1H NMR: 8.50 (dd,J=4.9, 1.5 Hz, 1H), 8.35 (d,J=2.0 Hz, 1H), 7.70 (dt,J=7.8, 2.0 Hz, 1H), 7.37-7.19 (m,9H), 7.14 (m,1H), 5.48 (d,J=1.0 Hz, 1H), 5.39 (d,J=1.0 Hz, 1H), 4.85 (s,2H), 3.09 (q,J=7.3 Hz, 2H), 1.41 (t,J=7.3 Hz, 3H). MS calcd. 378.1; MS (M+1) 379.1.

Workup

  1. extractionExtracted with EtOAc
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed with 10:1 to 5:1 DCM/EtOAc

Sources & evidence

ORD record
ord-2f971c401d45486cb7bdbe9893cf3827
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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