Hydrogen Peroxide → 5-(Benzenesulfinyl)-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 1991098Notes

Reaction equation

HRID 1991098 reaction equation
[C:1]1([S:7][C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:18]=[N:19][NH:20][CH:21]=4)=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:22]O>C(O)(=O)C>[C:1]1([S:7]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:21]=[N:20][NH:19][CH:18]=4)=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)=[O:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 160647935-(Phenylsulfanyl)-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 160647975-(Benzenesulfinyl)-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 64.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of sulfide 8 (20 mg, 0.068 mmol) and 30% aqueous H2O2 (10.5 μL, 0.103 mmol) in glacial acetic acid (224 μL) was stirred for 72 h then purified by preparative LCMS (column LUNA 10 μl C18(2) 00G-4253-V0 250×50 mm) using water—acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to give sulfoxide 9 as a white solid (13.6 mg, 64%); 1H NMR (400 MHz, CDCl3+6 drops CD3OD) δ 7.35-7.50 (m, 4H), 7.60 (m, 2H), 7.78 (s, 2H), 8.35 (d, J=2.0 Hz, 1H), 8.40 (d, J=2.0 Hz, 1H).

Workup

  1. customthen purified by preparative LCMS (column LUNA 10 μl C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-ddcd10eb2c74434f9f7ca76c00cdbf30
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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