Boron tribromide → HCID 136098511, compound

HRID 1627658Notes

Reaction equation

HRID 1627658 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[C:20]([C:21]([F:24])([F:23])[F:22])=[N:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:25]C)[CH:17]=2)[N:12]=1)[C:5]([OH:7])=[O:6].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[C:20]([C:21]([F:23])([F:24])[F:22])=[N:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:25])[CH:17]=2)[N:12]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67974881HCID 67974881, compound

Product 1

HCID 136098511HCID 136098511, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 3-chloro-4-(6-methoxy-3-(trifluoromethyl)quinoxalin-2-yl)benzoic acid (150 mg, 0.392 mmol) and BBr3 (3 mL) in anhydrous DCM (30 mL) was stirred at 25° C. overnight. The resulting mixture was quenched with water (30 mL), extracted with EtOAc (50 mL×3), dried over Na2SO4 and concentrated in vacuo. The residue was purified by prep-HPLC (0.1% TFA as additive) to give Compound VI-1 (26 mg, yield 18%) as a solid. 1H NMR (DMSO-d6 400 MHz): δ 11.22 (brs, 1H), 8.14 (d, J=9.2 Hz, 1H), 8.10 (d, J=1.6 Hz, 1H), 8.04 (dd, J=8.0, 1.6 Hz, 1H), 7.77 (d, J=8.0 Hz, 1H), 7.70 (dd, J=9.2, 1.8 Hz, 1H), 7.47 (d, J=1.8 Hz, 1H). MS (ESI): m/z 369.0 [M+H]+.

Workup

  1. customThe resulting mixture was quenched with water (30 mL)
  2. extractionextracted with EtOAc (50 mL×3)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by prep-HPLC (0.1% TFA as additive)
  6. customto give Compound VI-1 (26 mg, yield 18%) as a solid

Sources & evidence

ORD record
ord-1c9b29c341a1444a9c7a31f11d57017c
Source dataset
uspto-grants-2014_07
Patent number
US08785643B2

Reaction notes

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