1,1-Dichloroethane → 8-Chloro-1,5-naphthyridin-3-ol

HRID 40365

반응식

HRID 40365 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([O:12]C)=[CH:7]2.B(Br)(Br)Br.ClC(Cl)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([OH:12])=[CH:7]2

참가 물질

5

반응물 3

HCID 63651,1-DichloroethaneHCID 25134Boron tribromideHCID 594273408-Chloro-3-methoxy-1,5-naphthyridine

생성물 1

HCID 1357435768-Chloro-1,5-naphthyridin-3-ol수율 56.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
60 °C

실험 절차

A pressure-resistant vial was charged with 8-chloro-3-methoxy-1,5-naphthyridine (2.5 g, 12.8 mmol), boron tribromide (13.4 mL, 141.3 mmol) and dichloroethane (0.6M, 21.4 mL). Vessel sealed and mixture stirred at 60° C. for 16 hrs. Next day the reaction mixture was chilled in ice bath and diluted with dichloromethane (200 mL). This was allowed to sit under nitrogen system until all fuming ceased. The resulting yellow solid material was then filtered and dried under high vacuum. This was suspended in 40% (90:10:1 DCM/MeOH/NH4OH)/DCM and purified in this system by ISCO silica gel chromatography (80 g) afford 8-chloro-1,5-naphthyridin-3-ol (1.3 g, 56% yield). MS [M+H]=181.2. Calc'd for C8H5ClN2O=180.59.

후처리

  1. customVessel sealed
  2. temperatureNext day the reaction mixture was chilled in ice bath
  3. filtrationThe resulting yellow solid material was then filtered
  4. customdried under high vacuum
  5. custompurified in this system by ISCO silica gel chromatography (80 g)

출처 및 근거

ORD 기록
ord-6f4a85c5f5fa432aa161793f77ea5d01
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524900B2

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