2,6-Dichloropyrazine → HCID 18186840, compound

HRID 1296637Notes

Reaction equation

HRID 1296637 reaction equation
[N:1]1([CH2:10][CH2:11][OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl:13][C:14]1[CH:19]=[N:18][CH:17]=[C:16](Cl)[N:15]=1>O1CCOCC1.ClCCl>[Cl:13][C:14]1[CH:19]=[N:18][CH:17]=[C:16]([O:12][CH2:11][CH2:10][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[N:15]=1

Participants

5

Reactant 2

HCID 785042,6-DichloropyrazineHCID 137349961H-Indole-1-ethanol

Product 1

HCID 18186840HCID 18186840, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

K-t-BuO (0.67 g, 5.93 mmol) was added to a stirred solution of the product obtained in step 1 above (0.67 g, 5.93 mmol) in dioxane (20 mL) at 0° C. (ice-bath). After being stirred for 7 min at 0° C. and 5 min at room temperature, the mixture was chilled to 0° C. (ice-bath) and 2,6-dichloropyrazine (2.62 g, 17.6 mmol) was added. The yellowish reaction mixture was stirred at 0° C. for 20 min and at room temperature for 10 min and then diluted with dichloromethane. Drying (K2CO3), filtration, and concentration in vacuo furnished a beige oil. This material was purified by chromatography on silica gel (13×4 cm) using n-hexane/ethyl acetate (80:20). This furnished 1.39 g (94%) of the title compound as an oil that solidified upon standing. HRMS m/z calcd for C14H12ClN3O (M)+ 273.0669, found 273.0671. Anal. (Cl4H12ClN3O) C, H, N.

Workup

  1. additionwas added
  2. customThe yellowish reaction mixture
  3. stirringwas stirred at 0° C. for 20 min and at room temperature for 10 min
  4. customDrying
  5. filtration(K2CO3), filtration, and concentration in vacuo
  6. customfurnished a beige oil
  7. customThis material was purified by chromatography on silica gel (13×4 cm)

Sources & evidence

ORD record
ord-d05ce829e7ed4f58ada289a0e6eebb7f
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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