Tetrahydrofuran → 1-[5-Fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethanamine

HRID 1192691Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])(=O)C.[NH4+:26].[Na].O1CCCC1>CO.C(#N)C>[F:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:26])[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1-[5-fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethanone (0.32 g, 1.1 mmol) and ammonium acetate (0.871 g, 11.3 mmol) in methanol (3.0 mL) and acetonitrile (3.0 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, to the resulting mixture was added 1.0 M sodium cyanoborohyride in tetrahydrofuran (2.8 mL, 2.8 mmol). The reaction was heated at 65° C. overnight, then cooled to room temperature and quenched with sat. NaHCO3 solution and extracted with dichloromethane. The combined extracts were dried over MgSO4 and evaporated to dryness. The residue was used directly in the next step. LCMS calculated for C17H15F2N2 (M+H)+: m/z=285.1; Found: 285.1.

Workup

temperatureAfter cooling to room temperature, to the resulting mixture
temperatureThe reaction was heated at 65° C. overnight
temperaturecooled to room temperature
customquenched with sat. NaHCO3 solution
extractionextracted with dichloromethane
dry with materialThe combined extracts were dried over MgSO4
customevaporated to dryness

Sources & evidence

ORD record: ord-69f45e4ef9c0478c90ff58f7181934fa
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

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