Sodium hydride → tert-Butyl 4-(1-(4-nitronaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamate

HRID 2069060Notes

Reaction equation

HRID 2069060 reaction equation
[OH:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:6]=1)[CH3:4].[H-].[Na+].F[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([N+:32]([O-:34])=[O:33])=[CH:24][CH:23]=1.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C([O-])(O)=O.[Na+]>CN(C=O)C.CO>[N+:32]([C:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22]([O:1][CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:6]=2)[CH3:4])=[CH:23][CH:24]=1)([O-:34])=[O:33]

Participants

8

Reactant 5

HCID 24758Sodium hydrideHCID 2617641-Fluoro-4-nitronaphthaleneHCID 516892Sodium BicarbonateHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 58532581tert-Butyl 4-(1-hydroxypropan-2-yl)pyridin-2-ylcarbamate

Product 1

HCID 58532579tert-Butyl 4-(1-(4-nitronaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of the alcohol (53) (0.62 g, 2.46 mmol) in DMF (4 mL) was added sodium hydride (60% dispersion in mineral oil, 0.246 g, 6.14 mmol) in a single portion and the mixture sonicated under a flow of nitrogen and then stirred at RT for 30 min. The resulting yellow suspension was cooled to 0° C. and a solution of 1-fluoro-4-nitronaphthalene (14) (0.470 g, 2.457 mmol) in DMF (2 mL) was added over 10 min. The reaction mixture was warmed to RT and glacial acetic (1.0 mL) was added. The mixture was poured onto saturated aqueous NaHCO3 solution and extracted with EtOAc. The organic layer was washed with saturated aqueous Na2CO3, solution, three times with water and twice with brine then dried (MgSO4) and evaporated in vacuo to give a yellow solid. The solid was suspended in MeOH (20 mL) and sonicated and the insoluble residue was collected by filtration and was washed with MeOH (10 mL) and then ether to afford the title compound (54) as an off white solid (0.73 g, 67%): m/z 424 (M+H)+ (ES+).

Workup

  1. customthe mixture sonicated under a flow of nitrogen
  2. temperatureThe resulting yellow suspension was cooled to 0° C.
  3. temperatureThe reaction mixture was warmed to RT
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with saturated aqueous Na2CO3, solution, three times with water and twice with brine
  6. dry with materialthen dried (MgSO4)
  7. customevaporated in vacuo
  8. customto give a yellow solid
  9. customsonicated
  10. filtrationthe insoluble residue was collected by filtration
  11. washwas washed with MeOH (10 mL)

Sources & evidence

ORD record
ord-7081f5447e124c298c7071e27417f9b6
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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