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

HRID 2067057Notes

Reaction equation

HRID 2067057 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-ylcarbamateYield 106.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-(2-hydroxyethyl)pyridin-2-ylcarbamate (11) (6.00 g, 25.2 mmol) in THF (70 mL) was added sodium hydride (2.52 g, 63.0 mmol, 60 wt %) at 0° C. The bright yellow suspension was stirred for 20 min at 0° C. before the addition of 1-fluoro-4-nitronaphthalene (4.81 g, 25.2 mmol) in a single portion. After stirring at RT for 2 hr, water (100 mL) was added followed by EtOAc (100 mL). The solid formed between the layers was collected by filtration and the organic phase was washed with saturated aq NaHCO3 (100 mL), brine (100 mL) and dried. The volatiles were removed to give an orange solid. The solids were combined and triturated from MeOH (50 mL) to give tert-butyl 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate (12) as a yellow solid (11.0 g, 98%): m/z 410 (M+H)+ (ES+).

Workup

  1. customThe solid formed between the layers
  2. filtrationwas collected by filtration
  3. washthe organic phase was washed with saturated aq NaHCO3 (100 mL), brine (100 mL)
  4. customdried
  5. customThe volatiles were removed
  6. customto give an orange solid
  7. customtriturated from MeOH (50 mL)

Sources & evidence

ORD record
ord-775edddd4cb143bc873a2112a81e4e75
Source dataset
uspto-grants-2012_10
Patent number
US08293748B2

Reaction notes

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