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

HRID 660484ノート

反応式

HRID 660484 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4f1c2406bffd4b44b9bdf4201bfe63b6
出典データセット
uspto-grants-2011_12
特許番号
US08084448B2

反応ノート

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