N-(2-Amino-5-methoxy-phenyl)-5-bromo-2-fluoro-benzamide → HCID 178488045, compound

HRID 77078Notes

Reaction equation

HRID 77078 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH:10][C:11](=O)[C:12]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:13]=1[F:19]>C(O)(=O)C>[Br:18][C:16]1[CH:15]=[CH:14][C:13]([F:19])=[C:12]([C:11]2[NH:1][C:2]3[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=3[N:10]=2)[CH:17]=1

Participants

3

Reactant 1

HCID 63257662N-(2-Amino-5-methoxy-phenyl)-5-bromo-2-fluoro-benzamide

Product 1

HCID 178488045HCID 178488045, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Method 6—Step b A mixture of N-(2-Amino-5-methoxy-phenyl)-5-bromo-2-fluoro-benzamide (1.45 g, 4.28 mmol) in acetic acid (15 mL) was heated at 80° C. overnight. Solvent was removed under reduced pressure and the crude purified by precipitation from AcOEt (20 mL), dried, recovered with a mixture of dichloromethane (20 mL) and methanol (1 mL) and washed with saturated NaHCO3 solution (3×5 mL), the organic layer recovered by filtration through phase separator, and the solvent removed under reduced pressure to obtain 0.86 g of the title compound (63%).

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe crude purified by precipitation from AcOEt (20 mL)
  3. customdried
  4. customrecovered with a mixture of dichloromethane (20 mL) and methanol (1 mL)
  5. washwashed with saturated NaHCO3 solution (3×5 mL)
  6. filtrationthe organic layer recovered by filtration through phase separator
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-1aa1f7824b264499a2831f4af1e1e42a
Source dataset
uspto-grants-2014_09
Patent number
US08835648B2

Reaction notes

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