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

HRID 595710ノート

反応式

HRID 595710 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-93aca5ad1a7b42b9bb3567a0b669f93d
出典データセット
uspto-grants-2016_01
特許番号
US09243002B2

反応ノート

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