Sodium methanesulfinate → HCID 86643713, compound

HRID 1098655Notes

Reaction equation

HRID 1098655 reaction equation
[NH2:1][CH:2]1[CH2:14][C:13]2[C:12]3[C:7](=[C:8](Br)[CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]=2[CH2:4][CH2:3]1.[CH3:22][S:23]([O-:25])=[O:24].[Na+]>CN1C(=O)CCC1.CCCCCCC.CCOC(C)=O>[NH2:1][CH:2]1[CH2:14][C:13]2[C:12]3[C:7](=[C:8]([S:23]([CH3:22])(=[O:25])=[O:24])[CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]=2[CH2:4][CH2:3]1

Participants

6

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 86643712HCID 86643712, compound

Product 1

HCID 86643713HCID 86643713, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of an appropriately protected ethyl (3-amino-8-bromo-1,2,3,4-tetrahydro-9H-carbazol-9-yl)-acetate derivative of Structure 2c (0.238 mmol), cuprous iodide (204 mg, 1.073 mmol, 4.5 eq.) and sodium methanesulfinate (129 mg, 1.073 mmol, 4.5 eq.) in degassed NMP (5 ml) is heated under inert atmosphere at 140° C. overnight. Then, the mixture is diluted with heptane (5 ml) and AcOEt (5 ml) and filtered over a pad of silica gel with AcOEt as eluent. The solvent is removed in vaccuo and the residue dissolved in AcOEt and H2O. The phases are separated and the aq. phase is extracted twice with AcOEt. The combined org. phases are washed with brine and H2O, dried over Na2SO4 and concentrated in vacuuo to yield the corresponding ethyl (3-amino-8-methanesulfonyl-1,2,3,4-tetrahydro-9H-carbazol-9-yl)-acetate derivative of Structure 1.

Workup

  1. filtrationfiltered over a pad of silica gel with AcOEt as eluent
  2. customThe solvent is removed in vaccuo
  3. dissolutionthe residue dissolved in AcOEt
  4. customThe phases are separated
  5. extractionthe aq. phase is extracted twice with AcOEt
  6. washphases are washed with brine and H2O
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuuo

Sources & evidence

ORD record
ord-dc05b7aeaed04f96b3104bb4e41a7072
Source dataset
uspto-grants-2012_03
Patent number
US08143304B2

Reaction notes

Loading…