Hexane → HCID 9899684, compound

HRID 902085Notes

Reaction equation

HRID 902085 reaction equation
Br[CH:2]([C:12]1[CH:17]=[N:16][CH:15]=[C:14]([CH3:18])[N:13]=1)[CH:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[CH:5]=1.C1CCN2C(=NCCC2)CC1.CCCCCC.C(OCC)(=O)C>C1COCC1>[F:10][C:6]1[CH:5]=[C:4]([C:3]#[C:2][C:12]2[CH:17]=[N:16][CH:15]=[C:14]([CH3:18])[N:13]=2)[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23500890HCID 23500890, compound

Product 1

HCID 9899684HCID 9899684, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[1,2-Dibromo-2-(3-fluorophenyl)ethyl]-6-methylpyrazine (2.97 g, 7.94 mmol) was dissolved in THF (40 mL), treated with DBU (8.7 mL, 63 mmol), and heated to reflux. After 16 h the reaction mixture was cooled, filtered, concentrated in vacuo, and purified by column chromatography eluting with 80:20 then 75:25 hexane:ethyl acetate to afford 2-[(3-fluorophenyl)ethynyl]-6-methylpyrazine (427 mg, 25% yield). This material was carried on to the salt formation without further purification.

Workup

  1. temperatureheated to reflux
  2. temperatureAfter 16 h the reaction mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography
  6. washeluting with 80:20

Sources & evidence

ORD record
ord-c8e37b6db3bd49d08ca9ecb0998fa545
Source dataset
uspto-grants-2008_04
Patent number
US07365074B2

Reaction notes

Loading…