m-Chloroperbenzoic acid → HCID 68486361, compound

HRID 1874941Notes

Reaction equation

HRID 1874941 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:9])=[C:4]([F:18])[C:3]=1[O:19][C:20]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[C:22]([Cl:28])[CH:21]=1.C1C=C(Cl)C=C(C(OO)=[O:37])C=1>ClCCl>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][NH:7][C:8]([C:10]2[N+:11]([O-:37])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:9])=[C:4]([F:18])[C:3]=1[O:19][C:20]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[C:22]([Cl:28])[CH:21]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59451472HCID 59451472, compound

Product 1

HCID 68486361HCID 68486361, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[4-Chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorobenzyl]pyridine-2-carboxamide (0.064 g, 0.154 mmol) in 4 mL of dichloromethane was added mCPBA (0.026 g, 0.154 mmol). The resulting mixture was stirred overnight at RT. The reaction mixture was washed with 15% Na2CO3 and the organic layer separated and evaporated. The solid was dissolved in DMF and diluted with MeOH to a volume of 2 mL. Purification was accomplished by reverse-phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.006 g, 9%) as a solid. 1H NMR (400 MHz, CDCl3) δ ppm 11.74-11.85 (m, 1H), 8.44 (dd, 1H), 8.26-8.30 (m, 1H), 7.46-7.52 (m, 1H), 7.40-7.45 (m, 1H), 7.32-7.38 (m, 2H), 7.24-7.29 (m, 1H), 7.16 (t, 1H), 7.01-7.04 (m, 1H), 4.74 (d, 2H). LCMS: m/z 431.9 (M+1).

Workup

  1. washThe reaction mixture was washed with 15% Na2CO3
  2. customthe organic layer separated
  3. customevaporated
  4. dissolutionThe solid was dissolved in DMF
  5. additiondiluted with MeOH to a volume of 2 mL
  6. customPurification

Sources & evidence

ORD record
ord-066fd849c2434a3390d56669eebf2a7e
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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