Selectfluor → HCID 86728240, compound

HRID 1776830Notes

Reaction equation

HRID 1776830 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.[F:18][B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2.F[B-](F)(F)F>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[F:18])=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:5]([OH:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 86728225HCID 86728225, compound

Product 1

HCID 86728240HCID 86728240, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-chloro-2-(1H-indol-2-yl)pyridin-3-ol (244 mg, 1 mmol) and 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane tetrafluoroborate (425 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 desired product of 6-chloro-2-(3-fluoro-1H-indol-2-yl)pyridin-3-ol (120 mg, yield: 46.2%). 1H-NMR (Methanol-d4, 400 MHz) δ 7.55 (d, J=8.0 Hz, 1H), 7.39˜7.44 (m, 1H), 7.25˜7.34 (m, 1H), 6.97˜7.20 (m, 3H). MS (M+H)+: 263/265.

Workup

  1. concentrationThe mixture was then concentrated
  2. custompurified

Sources & evidence

ORD record
ord-f2a0e509d1584686ae11920be48a6171
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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