Sodium Bicarbonate → 2-(6-chloro-3-(2-chloroethyl)pyridazin-4-yl)-4-fluoro-1H-indole

HRID 595710Notes

Reaction equation

HRID 595710 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]=[CH2:9])=[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)[CH:3]=1.C([O-])(O)=O.[Na+].[ClH:25].O1CCOCC1>>[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH2:8][CH2:9][Cl:25])=[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)[CH:3]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 903335012-(6-chloro-3-vinylpyridazin-4-yl)-4-fluoro-1H-indole

Product 1

HCID 903339492-(6-chloro-3-(2-chloroethyl)pyridazin-4-yl)-4-fluoro-1H-indoleYield 66%

Procedure

A solution of 2-(6-chloro-3-vinylpyridazin-4-yl)-4-fluoro-1H-indole (80 mg, 0.29 mmol) in HCl-dioxane (5 mL) was stirred at 50° C. After 15 minutes, NaHCO3 (a.q) was added. The mixture was extracted with DCM. The organic phase was dried over Na2SO4. After being concentrated in vacuo, the residue was purified by prep-TLC (DCM) to give the product of 2-(6-chloro-3-(2-chloroethyl)pyridazin-4-yl)-4-fluoro-1H-indole (60 mg, yield: 66%). 1H-NMR (CDCl3, 400 MHz) δ 9.04 (s, 1H), 7.63 (s, 1H), 7.28˜7.31 (m, 1H), 7.22˜7.26 (m, 1H), 6.99 (d, J=1.6 Hz, 1H), 6.84˜6.93 (m, 1H), 4.24 (t, J=6.4 Hz, 2H), 3.66 (t, J=6.5 Hz, 2H). MS (M+H)+: 310/312.

Workup

  1. extractionThe mixture was extracted with DCM
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationAfter being concentrated in vacuo
  4. customthe residue was purified by prep-TLC (DCM)

Sources & evidence

ORD record
ord-93aca5ad1a7b42b9bb3567a0b669f93d
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

Loading…