Dimethylformamide → tert-Butyl (6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)carbamate

HRID 1363079Notes

Reaction equation

[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][N:21](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:20]#[N:21])[CH:15]=2)[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 1B (250 mg, 0.76 mmol) and zinc cyanide (88 mg, 0.75 mmol) in DMF (2.5 mL) was bubbled with argon for 10 min, then tetrakis-(triphenylphosphine)palladium(0) (65 mg, 0.057 mmol) was added and the solution was deoxygenated. The reaction mixture was then heated at 90° C. for 4 h, cooled to RT, and partitioned between EtOAc and water. The aqueous layer was separated and extracted with EtOAc (2×20 mL). The combined EtOAc extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc (0 to 60%) in hexane to give the title compound (140 mg, 67% yield) as a white solid.

Workup

customthe solution was deoxygenated
temperaturecooled to RT
custompartitioned between EtOAc and water
customThe aqueous layer was separated
extractionextracted with EtOAc (2×20 mL)
washThe combined EtOAc extracts were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue was chromatographed (silica gel)
washeluting with EtOAc (0 to 60%) in hexane

Sources & evidence

ORD record: ord-462ebaaec18441b3bcd77b6b34837353
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884113B2

Reaction notes

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