1,2-Dichloroethane → 7-bromo-1-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-2-(chloromethyl)-1H-imidazo[4,5-c]quinoline

HRID 549190Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:13][C@@H:14]([CH3:24])[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Cl:25][CH2:26][CH2:27]Cl.Cl.ClCC(=N)OCC.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:13]([C@@H:14]([CH3:24])[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19])[C:27]([CH2:26][Cl:25])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A 1-L, three-necked, Morton flask, equipped with overhead stirrer, was charged with 7-bromo-N4-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)quinoline-3,4-diamine (33.4 g, 81.0 mmol) and 1,2-dichloroethane (400 mL) and the mixture was stirred under N2. Ethyl 2-chloroethanimidoate hydrochloride (29.1 g, 184.0 mmol) was then added in portions and the reaction mixture was heated to 70° C. for 3 days. The reaction mixture was then cooled to ambient temperature and treated with CHCl3 (500 mL) and saturated aqueous NaHCO3 solution (700 mL). The layers were separated and the organic portion was concentrated under reduced pressure to give 38 g of 7-bromo-1-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-2-(chloromethyl)-1H-imidazo[4,5-c]quinoline as a golden solid.

Workup

temperatureThe reaction mixture was then cooled to ambient temperature
customThe layers were separated
concentrationthe organic portion was concentrated under reduced pressure

Sources & evidence

ORD record: ord-a6186b9d3a18488599bdb6ee0da96cbe
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943609B2

Reaction notes

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