Potassium Carbonate → Tert-butyl 4-(2-methyl-4-nitrophenoxy)pyridin-2-ylcarbamate

HRID 240552Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=1.F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1[CH3:26].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:26][C:18]1[CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:17]=1[O:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of tert-butyl 4-hydroxypyridin-2-ylcarbamate (4.12 g, 19.6 mmol) and 1-fluoro-2-methyl-4-nitrobenzene (3.34 g, 21.6 mmol) in DMF (40 mL) was added K2CO3 (4.06 g, 29.04 mmol). After heating to 65° C. for 64 hours, the mixture was cooled to room temperature and poured into ice water (200 mL). The reaction mixture was extracted several times with ethyl acetate. The combined organics were concentrated under reduced pressure. The residue was chromatographed (20% ethyl acetate in hexanes) to provide the product (2.03 g, 30%).

Workup

temperaturethe mixture was cooled to room temperature
extractionThe reaction mixture was extracted several times with ethyl acetate
concentrationThe combined organics were concentrated under reduced pressure
customThe residue was chromatographed (20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-78620a617fd748c29ce9748025b19eeb
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648087B2

Reaction notes

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