Pyridine → 4-Fluorobenzamide

HRID 1071948Notes

Reaction equation

HRID 1071948 reaction equation
[N:1]1C=CC=C(OC2C=C(C=C(C#N)C=2)N)C=1.N1C=CC=CC=1.[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>C(Cl)Cl>[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH2:1])=[O:29])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 678794-Fluorobenzoyl chlorideHCID 22136195HCID 22136195, compound

Product 1

HCID 715724-Fluorobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Formula I where R1 is Pyridin-3-yl, R2 is CN, and R3 is 4-Fluorophenyl To a solution of 1 eq. (0.1 g, 0.473 mmol) of 3-(pyridin-3-yloxy)-5-cyano-aniline in 0.47 M in CH2Cl2 (1 mL) and 1.6 eq. of pyridine (0.56 g, 0.71 mmol) was added 3 eq. of 4-fluorobenzoyl chloride (0.225 g, 1.42 mmol) and the resultant mixture stirred at rt overnight. The reaction mixture was diluted with CH2Cl2, washed with sat. NaHCO3, dried (Na2SO4) and concentrated in vacuo. The resultant residue was diluted with toluene and concentrated in vacuo (5 times). Purification by chromatography over silica with 5% MeOH/CH2Cl2 as the eluant afforded 134 mg of a the desired title compound of Formula I, N-[3-cyano-5-(pyridin-3-yloxy)-phenyl]]-4-fluoro-benzamide, as a solid (85% yield). Mpt 169-172° C. MS (M−1) 332.3.

Workup

  1. washwashed with sat. NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. additionThe resultant residue was diluted with toluene
  5. concentrationconcentrated in vacuo (5 times)
  6. customPurification by chromatography over silica with 5% MeOH/CH2Cl2 as the eluant

Sources & evidence

ORD record
ord-0d3ea65cfb6c4f569dfc9f82ccfcd4d4
Source dataset
uspto-grants-2005_06
Patent number
US06908923B2

Reaction notes

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