Methanol → HCID 23614996, compound

HRID 1768455Notes

Reaction equation

HRID 1768455 reaction equation
CO[C:3]([C:5]1[C:6]2[NH:7][C:8](=[O:27])[C:9]([CH3:26])([CH3:25])[NH:10][C:11]=2[CH:12]=[CH:13][C:14]=1[C:15]1[C:20]([O:21]C)=[CH:19][CH:18]=[CH:17][C:16]=1[O:23]C)=[O:4].B(Br)(Br)Br.CO>C(Cl)Cl>[OH:23][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[C:14]1[C:5](=[C:6]3[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH3:25])([CH3:26])[C:8](=[O:27])[NH:7]3)[C:3](=[O:4])[O:21]2

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 69507304HCID 69507304, compound

Product 1

HCID 23614996HCID 23614996, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Quinoxalinone vii (420 mg, 1.14 mmol) was dissolved in dry CH2Cl2 (10 mL) and cooled to −78° C. under an atmosphere of N2. BBr3 (536 μL, 5.68 mmol) was added dropwise. After the addition, the reaction mixture was warmed to room temperature and stirred for 2 h. The mixture was cooled to −78° C. and MeOH (3 mL) was added to quench the reaction. The mixture was concentrated under reduced pressure and then diluted with water (30 mL) and extracted with EtOAc (7×50 mL). The organic layers were combined and solvent was removed under reduced pressure to provide crude product (350 mg) as a yellow solid. A small portion of the crude material was purified by reverse phase preparative HPLC for characterization, the rest of the crude was used directly for the next step without any further purification. 1H NMR (CD3OD) δ 8.74 (d, J=9 Hz, 1H), 7.14 (d, J=9 Hz, 1H), 7.13 (t, J=9 Hz, 1H), 6.74 (d, J=9 Hz, 1H), 6.72 (d, J=9 Hz, 1H), 1.33 (s, 6H). Anal. Calcd for C17H14N2O4 ⅙CF3COOH: C, 63.22; H, 4.34; N, 8.51. Found: C, 63.54; H, 4.50; N, 8.32.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was warmed to room temperature
  3. temperatureThe mixture was cooled to −78° C.
  4. customto quench
  5. customthe reaction
  6. concentrationThe mixture was concentrated under reduced pressure
  7. additiondiluted with water (30 mL)
  8. extractionextracted with EtOAc (7×50 mL)
  9. customsolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3134105809014341bef09a89f3cd9b1b
Source dataset
uspto-grants-2007_06
Patent number
US07235662B2

Reaction notes

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