Sodium hydride → HCID 67966854, compound

HRID 1916844Notes

Reaction equation

HRID 1916844 reaction equation
[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].[H-].[Na+].Cl[S:22]([C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1)(=[O:24])=[O:23]>CN(C=O)C.CCOC(C)=O>[C:14]([O:13][C:12]([N:11]([C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[C:2]=1[CH3:1])[S:22]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:33][CH:34]=1)(=[O:24])=[O:23])=[O:18])([CH3:15])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 4738388Methyl 4-(Chlorosulfonyl)benzoateHCID 67966849HCID 67966849, compound

Product 1

HCID 67966854HCID 67966854, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 1-E (0.174 g, 0.703 mmol) in DMF (5 mL), cooled to 0° C., was added 60% NaH (0.028 g, 0.703 mmol) and the reaction mixture was stirred at 0° C. for 20 min. Methyl 4-(chlorosulfonyl)benzoate (0.247 g, 1.06 mmol) was added in one-portion and the reaction mixture was stirred at ambient temperature for 2 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 1-F as a white solid (0.188 g, 60%). 1H-NMR (CDCl3): δ 8.22-8.35 (dd, 2H), 7.90-7.92 (d, 1H), 7.61-7.64 (d, 1H), 7.22-7.24 (m, 1H), 6.90-6.93 (m, 1H), 3.98 (s, 3H), 2.55 (s, 3H), 1.32 (s, 9H); MS: m/z 446.1 (MH+).

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 2 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-eb73049b28d74eada92d2786570f6878
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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