Sodium hydride → Methyl 3-(3,6-Dibromo-9H-carbazol-9-yl)-2-hydroxypropanoate

HRID 1911580Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[H-].[Na+].[C:18]([O:23][CH3:24])(=[O:22])[CH:19]1[O:21][CH2:20]1>CN(C=O)C>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:20][CH:19]([OH:21])[C:18]([O:23][CH3:24])=[O:22])[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3

Participants

Conditions

Temperature: 0 °C

Procedure

3,6-Dibromocarbazole (0.300 g, 0.923 mmol) was dissolved in DMF (1.2 mL) and cooled to 0° C. NaH (60% dispersion in mineral oil, 0.074 g, 1.846 mmol) was added and the reaction stirred for 1 h at 0° C. Methyl glycidate (0.471 g, 4.615 mmol) was added and the reaction was stirred and warmed to ambient temperature over 3.5 h. Upon completion by TLC the reaction mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted 3× with EtOAc, and the combined organics were washed with saturated aqueous NaCl, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane) to afford the desired product (125 mg, 32%).

Workup

stirringthe reaction was stirred
temperaturewarmed to ambient temperature over 3.5 h
customUpon completion by TLC the reaction mixture was partitioned between EtOAc and H2O
extractionThe aqueous layer was extracted 3× with EtOAc
washthe combined organics were washed with saturated aqueous NaCl
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane)

Sources & evidence

ORD record: ord-ff1307b1631d4c2f8022f13736489d7a
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604074B2

Reaction notes

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