Pyridine → Methyl 4-(2-(4-fluoro-2-methoxyphenoxy)phenylcarbamoyl)benzoate

HRID 1946585Notes

Reaction equation

HRID 1946585 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[NH2:9])=[C:4]([O:16][CH3:17])[CH:3]=1.Cl[C:19]([C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1)=[O:20].N1C=CC=CC=1>C1C=CC=CC=1.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[NH:9][C:19]([C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=2)=[O:20])=[C:4]([O:16][CH3:17])[CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 597837992-(4-Fluoro-2-methoxyphenoxy)aniline

Product 1

HCID 59783739Methyl 4-(2-(4-fluoro-2-methoxyphenoxy)phenylcarbamoyl)benzoateYield 94.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolvent

Procedure

To a slurry of title compound 91 (4 g, 17.15 mmol) and methyl 4-(chlorocarbonyl)benzoate (3.58 g, 18.01 mmol) in benzene (60 mL) at 0° C. was added pyridine (4.85 mL, 60.0 mmol) drop wise followed by a single crystal of DMAP. The temperature was raised to room temperature and the reaction mixture was left to stir for 1 h. The reaction mixture was filtered and the filtrate was diluted with 5% aq HCl and ethyl acetate. The organic layer was washed with 5% aq HCl, water and brine then left in the fridge over the weekend. The precipitated solid was filtered, washed with water and hexanes to afford title compound 92 (6.38 g, 94%) as an off-white solid. LRMS (ESI): (calc) 395.12 (found) 396.4 (MH)+.

Workup

  1. waitthe reaction mixture was left
  2. filtrationThe reaction mixture was filtered
  3. additionthe filtrate was diluted with 5% aq HCl and ethyl acetate
  4. washThe organic layer was washed with 5% aq HCl, water and brine
  5. waitthen left in the fridge over the weekend
  6. filtrationThe precipitated solid was filtered
  7. washwashed with water and hexanes

Sources & evidence

ORD record
ord-649b42c0b8c84597bd4d53061ca6f744
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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