Boron tribromide → HCID 43358068, compound

HRID 1992303Notes

Reaction equation

HRID 1992303 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]([NH:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]([O:21]C)=[O:20])=[O:12].B(Br)(Br)Br>C(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]([NH:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]([OH:21])=[O:20])=[O:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 24493354HCID 24493354, compound

Product 1

HCID 43358068HCID 43358068, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3-[(2-quinoxalinylcarbonyl)amino]-2-thiophenecarboxylate (0.5 g, 1.6 mmol) was dissolved in CH2Cl2 (100 mL) at 0° C. and BBr3 (4.8 mL, 1M solution in CH2Cl2) was added dropwise. The solution was stirred at room temperature overnight. The reaction was quenched with NH4Cl at 0° C. The organic layer washed with NaHCO3 and separated. The resulting organic layer was treated slowly with dil HCl until the solution became acidic. The mixture was concentrated and redissolved in EtOAc. This solution washed with water, The solvent was removed under reduced pressure and the crude product was re-crystallized from methanol to give the desired product (0.2 g, 42%). HPLC/MS: (M+H)+ 300.1 m/z. Retention time (LC-MS)=2.65 min. 1H NMR (DMSO-D6): 13.75 (s, 1H, broad); 12.43(s, 1H); 9.61(s, 1H); 8.26(m, 2H); 8.17(m, 1H); 8.07(m, 2H); 7.99(d, 1H).

Workup

  1. customThe reaction was quenched with NH4Cl at 0° C
  2. washThe organic layer washed with NaHCO3
  3. customseparated
  4. additionThe resulting organic layer was treated slowly with dil HCl until the solution
  5. concentrationThe mixture was concentrated
  6. dissolutionredissolved in EtOAc
  7. washThis solution washed with water
  8. customThe solvent was removed under reduced pressure
  9. customthe crude product was re-crystallized from methanol

Sources & evidence

ORD record
ord-5fc67819888f4ae28f94b733fc9de78e
Source dataset
uspto-grants-2010_01
Patent number
US07648986B2

Reaction notes

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