Sodium hydride → HCID 53822033, compound

HRID 1422255Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[N:11][C:10]2[C:5](=[CH:6][C:7]([N+:17]([O-:19])=[O:18])=[CH:8][C:9]=2[CH2:15][OH:16])[N:4]=1.[H-].[Na+].[C:22]([O:26][C:27](=[O:30])[CH2:28]Br)([CH3:25])([CH3:24])[CH3:23]>O1CCCC1>[C:22]([O:26][C:27](=[O:30])[CH2:28][O:16][CH2:15][C:9]1[CH:8]=[C:7]([N+:17]([O-:19])=[O:18])[CH:6]=[C:5]2[C:10]=1[N:11]=[C:12]([O:13][CH3:14])[C:3]([O:2][CH3:1])=[N:4]2)([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

300 mg (1.13 mmol) of 2,3-dimethoxy-5-hydroxymethyl-7-nitro-quinoxaline are placed in 8 ml of tetrahydrofuran and cooled to 0° C. 52 mg (1.05 equiv.) of approximately 55% NaH in oil are added and the mixture is stirred for 30 minutes at 0° C. 0.2 ml (1.5 equiv.) of bromo-acetic acid tert-butyl ester is added and after 20 minutes the ice-bath is removed. The reaction mixture is stirred at room temperature for 20 hours, diluted with water and extracted with ethyl acetate. The combined organic phases are washed once with brine, dried over magnesium sulfate and concentrated by evaporation. The residue is chromatographed (SiO2, ethyl acetate/petroleum ether 1:3) and the title compound is obtained in the form of a solid (340 mg).

Workup

customis removed
stirringThe reaction mixture is stirred at room temperature for 20 hours
additiondiluted with water
extractionextracted with ethyl acetate
washThe combined organic phases are washed once with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated by evaporation
customThe residue is chromatographed (SiO2, ethyl acetate/petroleum ether 1:3)

Sources & evidence

ORD record: ord-6cb7bf4f174d4a19a4d0a817a81335d7
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06080743

Reaction notes

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