Chlorosuccinimide → 4-Chloro-1, 7-dimethyl-6-(phenylsulfonyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine

HRID 628450Notes

Reaction equation

[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[N:11]([S:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)(=[O:17])=[O:16])[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[Cl:24]N1C(=O)CCC1=O>ClCCCl.CO>[Cl:24][C:10]1[C:5]2[N:6]([C:2]([CH3:1])=[N:3][N:4]=2)[C:7]2[CH:13]=[C:12]([CH3:14])[N:11]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C:8]=2[CH:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 1,7-dimethyl-6-(phenylsulfonyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (2.0 g, 6.1 mmol, from Step 4) and N-chlorosuccinimide (0.91 g, 6.8 mmol, Aldrich) in 1,2-dichloroethane (40 mL) was heated at 60° C. overnight. Flash chromatography, eluting with a gradient from 0-5% MeOH/DCM (0.5% NH4OH), afforded an orange solid which was refluxed in 10 mL MeOH for 15 minutes. The product was isolated by filtration. Yield: (2.2 g, 80%). 1H NMR (500 MHz, d6-DMSO) δ 8.23 (s, 1H), 8.01-7.96 (m, 2H), 7.80-7.74 (m, 1H), 7.68-7.61 (m, 2H), 7.22 (s, 1H), 2.86 (s, 3H), 2.62 (s, 3H); LCMS (M+H)+: 361.

Workup

washFlash chromatography, eluting with a gradient from 0-5% MeOH/DCM (0.5% NH4OH)
customafforded an orange solid which
customThe product was isolated by filtration

Sources & evidence

ORD record: ord-b62190e69d8e4edbbedb5ee395b407fb
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309246B2

Reaction notes

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