1,4-Dioxane hydrochloride → 2-(5-bromo-2-(2-chloroethyl)pyridin-3-yl)-4-fluoro-1H-indole

HRID 595681Notes

Reaction equation

HRID 595681 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[C:16]([F:19])[CH:15]=[CH:14][CH:13]=3)[C:5]([CH:8]=[CH2:9])=[N:6][CH:7]=1.[ClH:20].O1CCOCC1>>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[C:16]([F:19])[CH:15]=[CH:14][CH:13]=3)[C:5]([CH2:8][CH2:9][Cl:20])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 903335732-(5-bromo-2-vinylpyridin-3-yl)-4-fluoro-1H-indole

Product 1

HCID 903335962-(5-bromo-2-(2-chloroethyl)pyridin-3-yl)-4-fluoro-1H-indoleYield 90%

Procedure

A solution of 2-(5-bromo-2-vinylpyridin-3-yl)-4-fluoro-1H-indole (800 mg, 2.52 mmol) in 20 mL of HCl/1,4-dioxane (4 mol/L) was heated at 80° C. for 2 hours and then the mixture was concentrated in vacuo to give the crude 2-(5-bromo-2-(2-chloroethyl)pyridin-3-yl)-4-fluoro-1H-indole (800 mg, yield: 90%) which was used directly in the next step without further purification. 1H-NMR (CDCl3, 400 MHz) δ 8.76 (s, 1H), 8.66 (s, 1H), 7.93 (s, 1H), 7.14˜7.22 (m, 2H), 6.73˜6.86 (m, 1H), 6.72 (s, 1H), 4.07˜4.10 (m, 2H), 3.35˜3.36 (m, 2H). MS (M+H)+: 353/355.

Workup

  1. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-50cb785e60b34438948c6df2e87d0efa
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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