Boron tribromide → HCID 178448739, compound

HRID 30972Notes

Reaction equation

HRID 30972 reaction equation
[CH2:1]([N:5]1[C:10](=[O:11])[C:9]([C:12]2[NH:13][S:14](=[O:25])(=[O:24])[C:15]3[CH:21]=[C:20]([O:22]C)[CH:19]=[CH:18][C:16]=3[N:17]=2)=[C:8]([OH:26])[C:7]([CH:27]([CH3:29])[CH3:28])=[N:6]1)[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([N:5]1[C:10](=[O:11])[C:9]([C:12]2[NH:13][S:14](=[O:25])(=[O:24])[C:15]3[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:16]=3[N:17]=2)=[C:8]([OH:26])[C:7]([CH:27]([CH3:28])[CH3:29])=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 178448740HCID 178448740, compound

Product 1

HCID 178448739HCID 178448739, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Butyl-5-hydroxy-6-isopropyl-4-(7-methoxy-1, 1-dioxo-1,2-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-2H-pyridazin-3-one (5e) (56 mg) was dissolved in 3 mL of methylene chloride. BBr3 (466 μL, 1.0 M in methylene chloride) was added and the mixture was stirred at room temperature for 1.5 hours. LC-MS result showed the incompletion of the reaction. BBr3 (0.5 mL, 1.0 M) was added and the reaction mixture was continued to shake at room temperature overnight. LC-MS confirmed that the reaction was close to completion. The reaction mixture was poured onto ice (10 mL), extracted with CHCl3 (20 mL×3). The organic layer was dried over MgSO4, filtered, concentrated under reduced pressure and further purified by flash chromatography on silica gel to give the desired product (5f) (42.2 mg) in 78.0% yield. 1H NMR (400 MHz, CDCl3): δ 7.46 (d, 1H, J=2.8 Hz), 7.16-7.26 (m, 2 H), 4.20 (t, 2H, J=7.2 Hz), 3.34 (m, J=6.8 Hz, 1H), 1.81 (m, 2H), 1.41 (m, 2H), 1.29 (d, 6H, J=6.8 Hz), 1.00 (t, 3H, J=7.4 Hz); LC-MS (ESI+): m/e=407.1 [M+1]+ (exact MS: 406.13).

Workup

  1. customLC-MS result
  2. customthe incompletion of the reaction
  3. waitto shake at room temperature overnight
  4. customwas close to completion
  5. additionThe reaction mixture was poured onto ice (10 mL)
  6. extractionextracted with CHCl3 (20 mL×3)
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customfurther purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f17c5e88cce94e94a4c4b6a4f94a6f69
Source dataset
uspto-grants-2008_09
Patent number
US07425552B2

Reaction notes

Loading…