Sodium ethoxide → HCID 89783405, compound

HRID 1056089Notes

Reaction equation

Cl.[NH2:2][C:3](=[NH:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[O-]CC.[Na+].Br[CH2:16][C:17]([C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[N:21]=[C:22]([F:30])[C:23]([CH3:29])=[N:24]2)=O>CCO>[NH2:10][C:3]1[NH:2][C:17]([C:19]2[CH:28]=[CH:27][CH:26]=[C:25]3[C:20]=2[N:21]=[C:22]([F:30])[C:23]([CH3:29])=[N:24]3)=[CH:16][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

A glass microwave reaction vessel was charged with ethyl 3-amino-3-iminopropanoate hydrochloride (1.248 g, 7.49 mmol, Tyger Scientific, Inc., Ewing, N.J.) in EtOH (5 mL) and the solution was cooled to 0° C. Sodium ethoxide (21% w/w solution in EtOH; 2.80 mL, 7.49 mmol) was added dropwise and a precipitate was formed. After 10 min, 2-bromo-1-(3-fluoro-2-methylquinoxalin-5-yl)ethanone (Example 126h; 1.06 g, 3.74 mmol) was added, and the reaction was stirred at RT for 3 h. The reaction was quenched with water and extracted with DCM. The combined organic layers were dried (MgSO4), filtered and concentrated. The residue was purified with silica gel chromatography (10-25% EtOAc in Hexanes) to give ethyl 2-amino-5-(3-fluoro-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (615 mg, 1.957 mmol, 52% yield) as an orange solid. MS (ESI, pos. ion) m/z: 315.0 (M+1).

Workup

customA glass microwave reaction vessel
customa precipitate was formed
customThe reaction was quenched with water
extractionextracted with DCM
dry with materialThe combined organic layers were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified with silica gel chromatography (10-25% EtOAc in Hexanes)

Sources & evidence

ORD record: ord-21857741e19c426f93d4920984fbc2c1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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