Chlorosuccinimide → 2-(5-(3-Chloro-6-fluoroimidazo[1,2-a]pyridin-2-yl)pyridin-3-yl)propan-2-ol

HRID 705071노트

반응식

HRID 705071 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[C:13]([C:17]([OH:20])([CH3:19])[CH3:18])[CH:14]=[N:15][CH:16]=3)[N:10]=2)[CH:7]=1.[Cl:21]N1C(=O)CCC1=O>C(#N)C>[Cl:21][C:8]1[N:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]2=[N:10][C:9]=1[C:11]1[CH:12]=[C:13]([C:17]([OH:20])([CH3:18])[CH3:19])[CH:14]=[N:15][CH:16]=1

참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 867303792-(5-(6-Fluoroimidazo[1,2-a]pyridin-2-yl)pyridin-3-yl)propan-2-ol

생성물 1

HCID 867303802-(5-(3-Chloro-6-fluoroimidazo[1,2-a]pyridin-2-yl)pyridin-3-yl)propan-2-ol

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of the title compound from Example 2 Step E (0.068 g, 0.251 mmol) in acetonitrile (1.25 ml) was added N-chlorosuccinimide (0.040 g, 0.301 mmol). The resulting mixture was stirred at room temperature for 2 hours, then concentrated under reduced pressure. The resulting residue was diluted with dichloromethane, washed with saturated aqueous sodium chloride solution, dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by flash chromatography on silica gel (100% ethyl acetate) provided the title compound: LCMS m/z 306.08 [M+H]+; 1H NMR (500 MHz, CDCl3) 9.23 (d, J=1.7 Hz, 1H), 8.78 (d, J=2.1 Hz, 1H), 8.51 (t, J=2.0 Hz, 1H), 8.08 (t, J=2.5 Hz, 1H), 7.65 (dd, J=9.3, 4.9 Hz, 1H), 7.24-7.20 (m, 1H), 2.02 (br s, 1H), 1.69 (s, 6H).

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionThe resulting residue was diluted with dichloromethane
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography on silica gel (100% ethyl acetate)

출처 및 근거

ORD 기록
ord-295967e22f0241fa8a025bc34b2b7e5d
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173873B2

반응 노트

불러오는 중…