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

HRID 2069027Notes

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

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 4-(2-hydroxyethyl)pyridin-2-ylcarbamate (20) (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. and the 1-fluoro-4-nitronaphthalene (14) (4.81 g, 25.2 mmol) added 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 solution (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 the title compound (21) as a yellow solid (11.0 g, 98%): m/z 410 (M+H)+ (ES+).

Workup

stirringAfter stirring at RT for 2 hr
customThe solid formed between the layers
filtrationwas collected by filtration
washthe organic phase was washed with saturated aq NaHCO3 solution (100 mL), brine (100 mL)
customdried
customThe volatiles were removed
customto give an orange solid
customtriturated from MeOH (50 mL)

Sources & evidence

ORD record: ord-2d462479c7394e26a130f9dc3bc5303d
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299073B2

Reaction notes

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