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

HRID 660484Notes

Reaction equation

HRID 660484 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4f1c2406bffd4b44b9bdf4201bfe63b6
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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