m-Chloroperbenzoic acid → 3-[2-(Methylsulfinyl)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridine

HRID 1159875Notes

Reaction equation

HRID 1159875 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=3)=[N:11][N:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=23)[CH:6]=[CH:5][N:4]=1.C1C=C(Cl)C=C(C(OO)=[O:35])C=1>C(Cl)Cl>[CH3:1][S:2]([C:3]1[N:8]=[C:7]([C:9]2[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=3)=[N:11][N:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=23)[CH:6]=[CH:5][N:4]=1)=[O:35]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 595114283-[2-(Methylthio)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridine

Product 1

HCID 595114013-[2-(Methylsulfinyl)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridineYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-[2-(methylthio)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridine (0.82 g, 2.26 mmol) in DCM (22 mL) is added a solution of 50% mCPBA (818 mg, 2.37 mmol) in DCM (6 mL) through an addition funnel. The reaction is stirred for 10 min and saturated aqueous NaHCO3 and the layers are separated. The aqueous layer is extracted with DCM, and the combined organic layers are dried over MgSO4, filtered and concentrated. The residue is purified by silica gel chromatography (50% EtOAC/hexanes eluant) to provide the product (567 mg) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 8.93 (d, 1H, J=6.8), 8.68 (d, 1H, J=5.6), 8.57 (d, 1H, J=8.8), 8.44 (s, 1H, 8.37-8.35 (m, 1H, 8.08 (d, 1H, J=7.6), 7.78 (t, 1H, J=8.0), 7.61-7.65 (m, 1H), 7.21-7.26 (m, 2H), 2.84 (s, 3H).

Workup

  1. customsaturated aqueous NaHCO3 and the layers are separated
  2. extractionThe aqueous layer is extracted with DCM
  3. dry with materialthe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel chromatography (50% EtOAC/hexanes eluant)

Sources & evidence

ORD record
ord-370984af655b4a56aade1074c284cee3
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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