Chlorosuccinimide → HCID 86728238, compound

HRID 1776827Notes

Reaction equation

HRID 1776827 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:5]([OH:17])=[CH:4][CH:3]=1.C1C(=O)N([Cl:25])C(=O)C1>CC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[Cl:25])=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:5]([OH:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86728225HCID 86728225, compound

Product 1

HCID 86728238HCID 86728238, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-chloro-2-(1H-indol-2-yl)pyridin-3-ol (244 mg, 1 mmol, described in Example 1) and NCS (160 mg, 1.2 mmol) in Acetone (2 mL) was stirred at room temperature for 1 hour. The mixture was then concentrated and purified using prep-TLC (petroleum ether:EtOAc=2:1) to provide 6-chloro-2-(3-chloro-1H-indol-2-yl)pyridin-3-ol (180 mg, yield: 64.7%). 1H-NMR (CDCl3, 400 MHz) δ 9.03 (s, 1H), 7.61 (d, J=7.6 Hz, 1H), 7.15˜7.36 (m, 5H), 6.20˜6.40 (br s, 1H). MS (M+H)+: 279/281.

Workup

  1. concentrationThe mixture was then concentrated
  2. custompurified

Sources & evidence

ORD record
ord-9cafc3c244de4fbe893c36bdc7708667
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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