Sodium hydride → HCID 67966859, compound

HRID 2178549Notes

Reaction equation

HRID 2178549 reaction equation
[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:5]2=[N:4][C:3]=1[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].[H-].[Na+].Cl[S:23]([C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1)(=[O:25])=[O:24]>CN(C=O)C.CCOC(C)=O>[C:15]([O:14][C:13]([N:12]([C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][N:6]2[C:2]=1[CH3:1])[S:23]([C:26]1[CH:27]=[CH:28][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:34][CH:35]=1)(=[O:25])=[O:24])=[O:19])([CH3:16])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 4738388Methyl 4-(Chlorosulfonyl)benzoateHCID 67966855HCID 67966855, compound

Product 1

HCID 67966859HCID 67966859, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 2-B (0.799 g, 3.06 mmol) in DMF (22 mL), cooled to 0° C., was added 60% NaH (0.147 g, 3.67 mmol) and the reaction mixture was stirred at 0° C. for 20 min. Methyl 4-(chlorosulfonyl)benzoate (2.15 g, 9.17 mmol) was added in small portions and the reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture was diluted with EtOAc, washed with H2O (2×), brine, dried over Na2SO4, filtered, and the solvent evaporated under reduced pressure to afford a crude solid. The crude material was purified by flash column chromatography (SiO2) eluting with a heptanes-EtOAc gradient to afford compound 2-C as a white solid (0.693 g, 49%). 1H-NMR (CDCl3): δ 8.38-8.40 (dd, 2H), 8.23-8.25 (dd, 2H), 7.75-7.77 (d, 1H), 7.00-7.02 (d, 1H), 6.79-6.83 (m, 1H), 3.98 (s, 3H), 2.51 (s, 3H), 1.59 (s, 3H), 1.34 (s, 9H); MS: m/z 460.2 (MH+).

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 18 h
  2. washwashed with H2O (2×), brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customto afford a crude solid
  7. customThe crude material was purified by flash column chromatography (SiO2)
  8. washeluting with a heptanes-EtOAc gradient

Sources & evidence

ORD record
ord-8464adbcde084cbf91f48ae0b652e89e
Source dataset
uspto-grants-2015_06
Patent number
US09067935B2

Reaction notes

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