Ammonium Chloride → HCID 66954483, compound

HRID 2096969Notes

Reaction equation

[CH3:1][Li].[Br:3][C:4]1[CH:5]=[C:6]2[NH:12][C:11](=[O:13])[C:10]3([CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]3)[C:7]2=[N:8][CH:9]=1.[Cl-].[NH4+]>O1CCCC1>[Br:3][C:4]1[CH:5]=[C:6]2[NH:12][C:11](=[O:13])[C:10]3([CH2:18][CH2:17][C:16]([OH:19])([CH3:1])[CH2:15][CH2:14]3)[C:7]2=[N:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyllithium (1.6 M in diethyl ether, 4.88 mL, 7.81 mmol) was added dropwise to a stirred solution of 6′-bromospiro[cyclohexane-1,3′-pyrrolo[3,2-b]pyridine]-2′,4(1′H)-dione (preparation 18, 1.00 g, 3.39 mmol) in tetrahydrofuran (30 mL) at −78° C. The mixture was warmed to 0° C. over 3 h and stirred overnight at ambient temperature. Additional methyllithium (1.6 M in diethyl ether, 4.24 mL, 6.78 mmol) was added dropwise at −78° C. and the mixture was warmed to ambient temperature stirred overnight at ambient temperature. Saturated aqueous ammonium chloride solution (20 mL) was added to the reaction and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated. Purification of the residue by flash chromatography (0.1% Et3N in 1:1 to 3:1 ethyl acetate/hexanes) gave the two pure isomers of the title compound.

Workup

temperaturethe mixture was warmed to ambient temperature
stirringstirred overnight at ambient temperature
extractionthe mixture was extracted with ethyl acetate
customThe organic layer was separated
washwashed with brine
dry with materialdried (MgSO4)
customevaporated
customPurification of the residue by flash chromatography (0.1% Et3N in 1:1 to 3:1 ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-e8c5ff1f399044e3ba4e55e35318120d
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450341B2

Reaction notes

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