(Diethylamino)sulfur trifluoride → HCID 23521698, compound

HRID 392433Notes

Reaction equation

HRID 392433 reaction equation
O[CH:2]([C:9]1[CH:10]=[C:11]([N:15]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCN(S(F)(F)[F:34])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:34][CH:2]([C:9]1[CH:10]=[C:11]([N:15]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 44335650HCID 44335650, compound

Product 1

HCID 23521698HCID 23521698, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3-(α-hydroxybenzyl)phenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine (0.106 g, 2.77 mmol) in DCM was added DAST (0.040 mL, 3.05 mmol). The reaction was stirred overnight and poured into saturated NaHCO3 solution and extracted with EtOAc, dried over MgSO4, filtered, and concentrated. The residue was chromatographed on silica gel with 2:1 DCM/EtOAc to give the title compound as a clear oil. 1H NMR: 8.47 (dd,J=4.9, 1.5 Hz, 1H), 8.33 (d,J=2.0 Hz, 1H), 7.63 (dt,J=7.8, 2.0 Hz, 1H), 7.38-7.28 (m,4H), 7.24-7.16 (m,6H), 4.89 (AofAB,d,J=14.8 Hz, 1H), 4.83 (BofABd,J=14.8 Hz, 1H), 3.07 (q,J=7.3 Hz, 2H), 1.40 (t,J=7.3 Hz, 3H). MS calcd. 384.1; MS (M+1) 385.1.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel with 2:1 DCM/EtOAc

Sources & evidence

ORD record
ord-4856d471bc504d5eb48e19553528c70a
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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