Tetrahydrofuran → Tert-butyl {5-[(5-aminopyridin-2-yl)oxy]-2-fluorophenyl}carbamate

HRID 2366784Notes

Reaction equation

HRID 2366784 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=2)=[CH:4][C:3]=1[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].O1CCCC1>CO.[C].[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH:4]=2)=[N:10][CH:11]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 86657971Tert-butyl {2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate

Product 1

HCID 86657970Tert-butyl {5-[(5-aminopyridin-2-yl)oxy]-2-fluorophenyl}carbamateYield 94%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A suspension of tert-butyl {2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate (3.49 g, 10 mmol) and 10% palladium-carbon (1.0 g) in methanol (20 mL)-tetrahydrofuran (20 mL) was vigorously stirred at room temperature overnight under a hydrogen atmosphere. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The to residue was poured into water (200 mL), and the mixture was extracted with ethyl acetate (100 mL×2). The ethyl acetate layers were combined and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was triturated with diethyl ether to give the title compound (3.00 g, 94%) as a colorless powder.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe to residue was poured into water (200 mL)
  4. extractionthe mixture was extracted with ethyl acetate (100 mL×2)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-058f5a923bcb4b40b7492acc6671f19b
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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