Potassium Carbonate → Tert-butyl{4-chloro-2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate

HRID 1800611Notes

Reaction equation

HRID 1800611 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12]([OH:14])[C:11]([Cl:15])=[CH:10][C:9]=1[F:16])([CH3:4])([CH3:3])[CH3:2].Cl[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=2)[C:11]([Cl:15])=[CH:10][C:9]=1[F:16])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 783082-Chloro-5-nitropyridineHCID 91597094tert-butyl N-(4-chloro-2-fluoro-5-hydroxyphenyl)carbamate

Product 1

HCID 91123393Tert-butyl{4-chloro-2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}carbamateYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl(4-chloro-2-fluoro-5-hydroxyphenyl)carbamate (6.70 g, 25.6 mmol), 2-chloro-5-nitropyridine (4.06 g, 25.6 mmol), potassium carbonate (3.89 g, 28.1 mmol) and N,N-dimethylformamide (70 mL) was stirred at room temperature for 30 min. To the reaction mixture was added aqueous ammonium chloride solution (100 mL), and the mixture was extracted with ethyl acetate (150 mL×3). The organic layers were combined, washed successively with water (100 mL) and saturated brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (4.52 g, 46%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (150 mL×3)
  2. washwashed successively with water (100 mL) and saturated brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-59336fb066a447a2acec6d24acd27464
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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