Pyridine → HCID 86672177, compound

HRID 1843049Notes

Reaction equation

HRID 1843049 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15].N1C=CC=CC=1>CC(C)=O>[F:12][C:4]1[CH:3]=[C:2]([NH:1][C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:15])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 21957875Methyl 4-amino-2-fluorobenzoate

Product 1

HCID 86672177HCID 86672177, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of methyl 4-amino-2-fluorobenzoate (800 mg, 4.6 mmol, 1.0 eq) in acetone (10 mL) was added phenyl chloroformate (0.6 mL, 4.6 mmol, 1.0 eq) and followed by pyridine (1.1 mL, 13.8 mmol, 3.0 eq) at 0° C. and stirred at RT for 1 h. The acetone in the RM was evaporated and diluted with water (50 mL) extracted with EtOAC (2×100 mL). The organic layer was washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and evaporated under vacuum. The crude product was washed with n-pentane to yield methyl 2-fluoro-4-(phenoxycarbonylamino)benzoate (1.2 g, 89.6%) as white solid (TLC: EtOAc/PE (2:3); Rf: 0.3).

Workup

  1. customThe acetone in the RM was evaporated
  2. additiondiluted with water (50 mL)
  3. extractionextracted with EtOAC (2×100 mL)
  4. washThe organic layer was washed with water (50 mL), brine (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under vacuum
  7. washThe crude product was washed with n-pentane

Sources & evidence

ORD record
ord-0d2b810e0ae344aa951ee52eabdb4680
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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