Tetrahydrofuran → 5-[(2-Chloroethyl)pyrazol-1-ylmethyl]-6,7-dichloro-2,3-dimethoxyquinoxaline

HRID 1957113Notes

Reaction equation

HRID 1957113 reaction equation
[ClH:1].ClCC[C:5]1[CH:6]=[N:7][NH:8][CH:9]=1.[H-].[Na+].Br[CH2:13][C:14]1[C:23]([Cl:24])=[C:22]([Cl:25])[CH:21]=[C:20]2[C:15]=1[N:16]=[C:17]([O:28][CH3:29])[C:18]([O:26][CH3:27])=[N:19]2.O1[CH2:34][CH2:33]CC1>>[Cl:1][CH2:33][CH2:34][CH:13]([N:8]1[CH:9]=[CH:5][CH:6]=[N:7]1)[C:14]1[C:23]([Cl:24])=[C:22]([Cl:25])[CH:21]=[C:20]2[C:15]=1[N:16]=[C:17]([O:28][CH3:29])[C:18]([O:26][CH3:27])=[N:19]2

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 105459165-Bromomethyl-6,7-dichloro-2,3-dimethoxyquinoxalineHCID 190688934-(2-chloroethyl)-1H-pyrazole hydrochloride

Product 1

HCID 543391965-[(2-Chloroethyl)pyrazol-1-ylmethyl]-6,7-dichloro-2,3-dimethoxyquinoxalineYield 63%

Conditions

Temperature
10 °C

Procedure

4-(2-Chloroethyl)pyrazole hydrochloride (250 mg, 1.0 mmol) was added to a suspension of sodium hydride (90 mg, 80% oil dispersion, 3.0 mmol) in dry tetrahydrofuran (10 mL) at 0° C. under nitrogen with stirring. Immediately 5-bromomethyl-6,7-dichloro-2,3-dimethoxyquinoxaline (352 mg, 1.0 mmol) was added, and the mixture was allowed to warm to 10° C. over 2 hours. The mixture was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic solution was dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography (gradient elution with ethyl acetate/hexane), followed by trituration with methanol gave 5-[(2-chloroethyl)pyrazol-1-ylmethyl]-6,7-dichloro-2,3-dimethoxyquinoxaline (254 mg, 63%), as a white solid.

Workup

  1. customThe mixture was partitioned between ethyl acetate (50 mL) and water (50 mL)
  2. dry with materialThe organic solution was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customPurification
  5. washby flash chromatography (gradient elution with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-200a6dfd31774c54a0d54b6b058b1f7f
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

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