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

HRID 595710노트

반응식

HRID 595710 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-93aca5ad1a7b42b9bb3567a0b669f93d
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

반응 노트

불러오는 중…