2-Bromo-6-(fluoromethyl)pyridine → 6-Fluoro-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)quinoxaline

HRID 422387Notes

Reaction equation

HRID 422387 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][F:9])[N:3]=1.[CH2:10]([C:14]1[CH:23]=[N:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([F:24])[CH:20]=2)[N:15]=1)[CH2:11][C:12]#[CH:13]>>[F:24][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH2:10][CH2:11][C:12]#[C:13][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][F:9])[N:3]=1)[CH:23]=[N:22]2

Participants

3

Reactant 2

HCID 102416102-Bromo-6-(fluoromethyl)pyridineHCID 860868782-But-3-ynyl-6-fluoro-quinoxaline

Product 1

HCID 665981276-Fluoro-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)quinoxalineYield 68.2%

Procedure

The title compound was prepared in accordance with the general method of Example 108(C), from 2-bromo-6-(fluoromethyl)-pyridine (43 mg, 0.22 mmol) and 2-but-3-ynyl-6-fluoro-quinoxaline (45 mg, 0.22 mmol). Microwave conditions: 120° C. for 15 minutes. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 3:2) to yield 45 mg (0.15 mmol, 65%) of 6-fluoro-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)quinoxaline as an orange solid with a purity of 85%.

Workup

  1. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 3:2)

Sources & evidence

ORD record
ord-9259d6b07d8c4361be8b5bf9a557be92
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

Loading…