Sodium hydride → HCID 58532572, compound

HRID 2069065Notes

Reaction equation

HRID 2069065 reaction equation
[OH:1][CH2:2][C:3]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:7]=1)([CH3:5])[CH3:4].[H-].[Na+].F[C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([N+:33]([O-:35])=[O:34])=[CH:25][CH:24]=1.C([O-])(O)=O.[Na+]>CN(C=O)C.C(O)(=O)C>[CH3:4][C:3]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:7]=1)([CH3:5])[CH2:2][O:1][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([N+:33]([O-:35])=[O:34])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 2617641-Fluoro-4-nitronaphthaleneHCID 516892Sodium BicarbonateHCID 58532557HCID 58532557, compound

Product 1

HCID 58532572HCID 58532572, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of the alcohol (59) (1.11 g, 4.17 mmol) in DMF (10.0 mL) at 0° C. under nitrogen was added sodium hydride (350 mg, 8.75 mmol) in a single portion. The mixture was warmed to RT for 30 min and was then sonicated, flushed with nitrogen and re-cooled to 0° C. A solution of 1-fluoro-4-nitronaphthalene (14) (797 mg, 4.17 mmol) in DMF (4.0 mL) was added over 5 min and the reaction mixture allowed to warm to RT and after 30 min glacial acetic acid (1.0 mL) was added. The reaction mixture was poured onto saturated aqueous NaHCO3 solution and extracted twice with EtOAc. The combined organic extracts were washed three times with water and with brine and then dried (MgSO4), and evaporated in vacuo. The residue was triturated from EtOAc and washed with ether (20 mL) to afford the title compound (60) as a yellow solid (1.23 g, 64%): m/z 438 (M+H)+ (ES+).

Workup

  1. customwas then sonicated
  2. customflushed with nitrogen
  3. temperaturere-cooled to 0° C
  4. additionwas added
  5. extractionextracted twice with EtOAc
  6. washThe combined organic extracts were washed three times with water
  7. dry with materialwith brine and then dried (MgSO4)
  8. customevaporated in vacuo
  9. customThe residue was triturated from EtOAc
  10. washwashed with ether (20 mL)

Sources & evidence

ORD record
ord-91a036174c47496085554db92d0e7330
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

Loading…