Methyl morpholine oxide → HCID 58107392, compound

HRID 873679Notes

Reaction equation

HRID 873679 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]3[CH3:22])=[C:12]([F:23])[CH:11]=2)[OH:9])=[CH:4][C:3]=1[S:24]([NH2:27])(=[O:26])=[O:25].C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:9])[C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]3[CH3:22])=[C:12]([F:23])[CH:11]=2)=[CH:4][C:3]=1[S:24]([NH2:27])(=[O:26])=[O:25]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66850709HCID 66850709, compound2×

Product 1

HCID 58107392HCID 58107392, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Following method B, 2-chloro-5-((4-(2,5-dimethyl-pyrrol-1-yl)-3-fluoro-phenyl)-hydroxy-methyl)-benzenesulfonamide is synthesized from the corresponding aryl bromide. In the next step, a solution of 100 ring of 2-chloro-5-((4-(2,5-dimethyl-pyrrol-1-yl)-3-fluoro-phenyl)-hydroxy-methyl)-benzenesulfonamide (0.24 mmol, 1 equivalent), 43 mg of 4-methylnnorpholine N-oxide, and 122 mg of 4 Å molecular sieves in 5 mL of dichloromethane is stirred at room temperature as 5 mg of tetrapropylammonium perruthenate is added. The reaction is stirred at room temperature for 1 h, then filtered through a pad of silica gel, eluted with ethyl acetate and concentrated in vacuo. After purification by flash chromatography, 45 mg of product is obtained. 1H NMR (400 MHz, CDCl3): δ 2.05 (s, 6H), 5.20 (s, 2H), 6.0 (s, 2H), 7.40 (t, 1H, J=8 Hz), 7.65-7.75 (m, 3H), 8.05 (dd, 1H, J=8 Hz), 8.55 (d, 1H, J=2 Hz). MS (m/z): 407 (M+1).

Workup

  1. additionis added
  2. filtrationfiltered through a pad of silica gel
  3. washeluted with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customAfter purification by flash chromatography

Sources & evidence

ORD record
ord-4d70201dd8a44039adaace373f123ccb
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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