Boron tribromide → HCID 10139080, compound

HRID 2303735Notes

Reaction equation

HRID 2303735 reaction equation
[Cl:1][C:2]1[C:3]([CH3:30])=[N:4][O:5][C:6]=1[NH:7][S:8]([C:11]1[CH:15]=[CH:14][S:13][C:12]=1[C:16](=[O:29])[CH2:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[C:20]([O:26]C)[C:19]=1[CH3:28])(=[O:10])=[O:9].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[C:3]([CH3:30])=[N:4][O:5][C:6]=1[NH:7][S:8]([C:11]1[CH:15]=[CH:14][S:13][C:12]=1[C:16](=[O:29])[CH2:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[C:20]([OH:26])[C:19]=1[CH3:28])(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10116024HCID 10116024, compound

Product 1

HCID 10139080HCID 10139080, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(4-chloro-3-methyl-5-isoxazolyl)-2-(2-(3-methoxy-2,4,6-trimethylphenyl)acetyl)-3-thiophenesulfonamide (Example 49) (50 mg, 0.107 mmol) in dichloromethane (20 mL) at 0° C. was added BBr3 (1 M in dichloromethane, 3 mL, 3.0 mmol). The resulting mixture was stirred at 0° C. for 1 h and at room temperature for 8 h before it was poured into crushed ice (˜100 g). The aqueous mixture was stirred until all ice melted and extracted with dichloromethane (2×100 mL). The organic layers were combined and concentrated, and the residue was purified by HPLC to give N-(4-chloro-3-methyl-5-isoxazolyl)-2-(2-(3-hydroxy-2,4,6-trimethylphenyl)acetyl)-3-thiophenesulfonamide (47 mg, 85%).

Workup

  1. additionwas poured
  2. stirringThe aqueous mixture was stirred until all ice
  3. extractionextracted with dichloromethane (2×100 mL)
  4. concentrationconcentrated
  5. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-1ecf299f87ab42bdb35f3f17881c05c4
Source dataset
uspto-grants-2002_08
Patent number
US06432994B1

Reaction notes

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