Water → tert-Butyl 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate

HRID 1774362Notes

Reaction equation

HRID 1774362 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=1.[H-].[Na+].F[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([N+:31]([O-:33])=[O:32])=[CH:23][CH:22]=1.O>C1COCC1.CCOC(C)=O>[N+:31]([C:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]([O:1][CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH:5]=2)=[CH:22][CH:23]=1)([O-:33])=[O:32]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2617641-Fluoro-4-nitronaphthaleneHCID 58416767tert-Butyl (4-(2-hydroxyethyl)pyridin-2-yl)carbamate

Product 1

HCID 58416756tert-Butyl 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-(2-hydroxyethyl)pyridin-2-ylcarbamate (6.0 g, 25 mmol) in THF (70 mL) at 0° C. was added sodium hydride (2.52 g, 60% wt dispersion in mineral oil, 63.0 mmol) and the bright yellow suspension stirred for 20 min and then treated with 1-fluoro-4-nitronaphthalene (4.81 g, 25.2 mmol) in a single portion. After stirring at RT for 2 hr the mixture was treated with water (100 mL) followed by EtOAc (100 mL) and the solid which formed at the interface was collected by filtration. The organic phase was separated and was washed with saturated aq. NaHCO3 and brine and was then dried and evaporated in vacuo to furnish an orange solid. The two solids were combined and triturated with MeOH (50 mL) to provide tert-butyl 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate, as a yellow solid (11.0 g, 98%): m/z 410 (M+H)+ (ES+).

Workup

  1. stirringAfter stirring at RT for 2 hr the mixture
  2. customthe solid which formed at the interface
  3. filtrationwas collected by filtration
  4. customThe organic phase was separated
  5. washwas washed with saturated aq. NaHCO3 and brine
  6. customwas then dried
  7. customevaporated in vacuo
  8. customto furnish an orange solid
  9. customtriturated with MeOH (50 mL)

Sources & evidence

ORD record
ord-ad2a93527511427f80f2e65e3080812a
Source dataset
uspto-grants-2016_02
Patent number
US09260410B2

Reaction notes

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