Boron tribromide → 5-[2-Hydroxy-4-((E)-2-pyridin-3-yl-vinyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660484노트

반응식

HRID 660484 반응식
C([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[CH:11][C:10]=1[N:23]1[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:30])[CH2:24]1)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[OH:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[CH:11][C:10]=1[N:23]1[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:30])[CH2:24]1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 688388735-[2-Benzyloxy-4-((E)-2-pyridin-3-yl-vinyl)-phenyl]1,1-dioxo-1,2,5-thiadiazolidin-3-one

생성물 1

HCID 249701815-[2-Hydroxy-4-((E)-2-pyridin-3-yl-vinyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-[2-benzyloxy-4-((E)-2-pyridin-3-yl-vinyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (52 mg, 0.123 mmol) in methylene chloride (2 mL) at 0° C. is added BBr3 (0.247 mL, 1M in methylene chloride, 0.247 mmol) slowly and the mixture is stirred for 30 min. The mixture is quenched with 1N HCl and extracted with EtOAc. A yellow precipitate forms in the aqueous layer and is filtered and dried under reduced pressure to give the title compound: (M−1)−=330; HPLC retention time=0.77 min (method A).

후처리

  1. customThe mixture is quenched with 1N HCl
  2. extractionextracted with EtOAc
  3. filtrationA yellow precipitate forms in the aqueous layer and is filtered
  4. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-4f1c2406bffd4b44b9bdf4201bfe63b6
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084448B2

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