Water → HCID 67193704, compound

HRID 401465Notes

Reaction equation

HRID 401465 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:30])=[C:6]([S:8]([N:11]([CH3:29])[N:12]=[CH:13][C:14]2[N:18]3[CH:19]=[C:20]([C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)(=[O:10])=[O:9])[CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:36].O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:30])=[C:6]([S:8]([N:11]([CH3:29])[N:12]=[CH:13][C:14]2[N:18]3[CH:19]=[C:20]([C:23]4[CH:24]=[N+:25]([O-:36])[CH:26]=[CH:27][CH:28]=4)[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)(=[O:9])=[O:10])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 70662697HCID 70662697, compound

Product 1

HCID 67193704HCID 67193704, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 5-fluoro-N, 2-dimethyl-N′-((6-(pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)methylene) benzenesulfonohydrazide (step 1, 18 mg, 0.043 mmol) in CH2Cl2 was added 3-chloroperoxybenzoic acid (14.46 mg, 0.065 mmol). The reaction mixture was stirred for 3 h at RT. The reaction mixture was then poured on to water. Organic layer was separated, washed with saturated solution of NaHCO3 and dried over Na2SO4. Crude compound was purified by column chromatography (silica gel, 5% EtOAc in petroleum ether) to obtain the title compound. Yield: 64%; 1H NMR (DMSO-d6; 300 MHz,): δ 9.45 (s, 1H), 8.57 (s, 1H), 8.32-8.31 (m, 2H), 8.03 (s, 1H), 7.83-7.79 (m, 2H), 7.67-7.64 (dd, 1H, J=8.4 Hz, 2.4 Hz), 7.56 (m, 1H), 7.43-7.36 (m, 3H), 3.40 (s, 3H), 2.54 (s, 3H); MS: m/z 440 (M+1)+.

Workup

  1. customOrganic layer was separated
  2. washwashed with saturated solution of NaHCO3
  3. dry with materialdried over Na2SO4
  4. customCrude compound was purified by column chromatography (silica gel, 5% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-6c7099b2698e4692a6fc5d53f20733b6
Source dataset
uspto-grants-2014_06
Patent number
US08741932B2

Reaction notes

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