Methanesulfonyl chloride → HCID 59226390, compound

HRID 2046813Notes

Reaction equation

HRID 2046813 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:15][C@H:14]([C:16]([F:19])([F:18])[F:17])[CH2:13][C@H:12](O)[CH:11]=1)([O-:3])=[O:2].CS(Cl)(=O)=O.[N-:26]=[N+:27]=[N-:28].[Na+]>C(Cl)Cl.C(OCC)(=O)C.CCCCCCC>[N:26]([C@H:12]1[CH2:13][C@@H:14]([C:16]([F:19])([F:18])[F:17])[CH2:15][C:10]([C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:11]1)=[N+:27]=[N-:28]

Participants

7

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 33557Sodium Azide2×HCID 59226606HCID 59226606, compound

Product 1

HCID 59226390HCID 59226390, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

To a solution of cis-3-(3-nitropyridin-4-yl)-5-(trifluoromethyl)cyclohex-2-enol (1.0 eq) in DCM (0.14 M) was added TEA (2.5 eq), and followed by MsCl (1.8 eq) at room temperature. The reaction mixture was stirred at room temperature for 2 hours. The solvent was removed. The residue was dissolved in DMF (0.19 M), and then the mixture was added sodium azide (1.2 eq). The resulting mixture was stirred at room temperature for 1 hour. Another 1.2 eq of sodium azide was added. The mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and heptane, and washed with sat NaCl. The organic was dried over MgSO4, filtered and concentrated. The residue was purified by column (1:1 ethyl acetate and hexanes) to give cis-4-(3-azido-5-(trifluoromethyl)cyclohex-1-enyl)-3-nitropyridine (58%). LC/MS (m/z): MH+=314.1, Rt=0.96 min.

Workup

  1. customThe solvent was removed
  2. dissolutionThe residue was dissolved in DMF (0.19 M)
  3. stirringThe resulting mixture was stirred at room temperature for 1 hour
  4. stirringThe mixture was stirred at room temperature overnight
  5. washwashed
  6. dry with materialThe organic was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column (1:1 ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-941fb6173e174f378fde33f70f519a4e
Source dataset
uspto-grants-2013_11
Patent number
US08592455B2

Reaction notes

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