Pyridine → 5-Benzyloxycarbonylamino-2-(2-methyl-imidazol-1-yl)fluorobenzene

HRID 8153

Reaction equation

HRID 8153 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH3:14])=[C:6]([F:8])[CH:7]=1.N1C=CC=CC=1.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:25]([O:24][C:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH3:14])=[C:6]([F:8])[CH:7]=1)=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 218766203-fluoro-4-(2-methyl-1H-imidazol-1-yl)aniline

Product 1

HCID 218766515-Benzyloxycarbonylamino-2-(2-methyl-imidazol-1-yl)fluorobenzeneYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Amino-2-(2-methylimidazol-1-yl)fluorobenzene (34.25 g, 0.179 M) was dissolved in dry dichloromethane (600 ml) under nitrogen, and cooled to −5°. Pyridine (17.7 g, 0.224 M) was added, followed by benzyl chloroformate (33.7 g, 0.197 M) over 20 minutes. The mixture was stirred and the temperature allowed to rise to ambient over 16 hours. Aqueous sodium bicarbonate (5%, 250 ml) was added, the organic layer separated, the aqueous layer re-extracted with dichloromethane (2×300 ml), and combined extracts dried (magnesium sulfate). After filtration and evaporation, the residue was recrystallised from toluene (400 ml) to give title product (54.5 g).

Workup

  1. temperaturecooled to −5°
  2. customthe organic layer separated
  3. extractionthe aqueous layer re-extracted with dichloromethane (2×300 ml)
  4. dry with materialdried (magnesium sulfate)
  5. filtrationAfter filtration and evaporation
  6. customthe residue was recrystallised from toluene (400 ml)

Sources & evidence

ORD record
ord-d9bb5586c23743ebb695b08c565f0db1
Source dataset
uspto-grants-2006_08
Patent number
US07087629B2

Linked notes

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