Phenol → Ethanesulfonic acid (3-phenoxymethyl-phenyl)-pyridin-3-ylmethyl-amide

HRID 392432Notes

Reaction equation

HRID 392432 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:32]1([OH:38])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.O[CH2:40][C:41]1[CH:42]=[C:43]([N:47]([CH2:53][C:54]2[CH:55]=[N:56][CH:57]=[CH:58][CH:59]=2)[S:48]([CH2:51][CH3:52])(=[O:50])=[O:49])[CH:44]=[CH:45][CH:46]=1>C1COCC1.CCOC(C)=O>[O:38]([CH2:40][C:41]1[CH:42]=[C:43]([N:47]([CH2:53][C:54]2[CH:55]=[N:56][CH:57]=[CH:58][CH:59]=2)[S:48]([CH2:51][CH3:52])(=[O:49])=[O:50])[CH:44]=[CH:45][CH:46]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 23521701n-(3-Hydroxymethylphenyl)-n-(ethylsulfonyl)pyrid-3-ylmethylamine

Product 1

HCID 23521708Ethanesulfonic acid (3-phenoxymethyl-phenyl)-pyridin-3-ylmethyl-amide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of triphenylphosphine (0.141 g, 0.539 mmol) in 3.5 mL THF was added diethylazodicarboxylate (0.165 g, 0.539 mmol). After 5 min phenol (0.061 g, 0.646 mmol) was added as a solution in 2 mL THF. After 5 min N-(3-(hydroxymethyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine (0.165 g, 0.539 mmol) was added as a solution in 2 mL THF and the reaction was stirred for 3 days. The mixture was diluted with EtOAc, washed with 1 N NaOH and brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel with 4:1 to 2:1 DCM/EtOAc to give the title compounds as a clear oil. 1H NMR: 8.48 (d,J=1.5 Hz, 1H), 8.36 (s,1H), 7.64 (d,J=7.8 Hz, 1H), 7.36-7.23 (m,5H), 7.19 (m,2H), 6.95 (t,J=7.8 Hz, 1H), 6.91 (d,J=7.8 Hz, 1H), 5.01 (s,2H), 4.84 (s,2H), 3.03 (q,J=7.6 Hz, 2H), 1.39 (t,J=7.6 Hz, 3H). MS calcd. 382.1; MS (M+1) 383.1.

Workup

  1. washwashed with 1 N NaOH and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel with 4:1 to 2:1 DCM/EtOAc

Sources & evidence

ORD record
ord-8b2b175ff6db430da398d9bd93cb3b9c
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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