Dabco → tert-Butyl 1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

HRID 269958Notes

Reaction equation

I[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].N12CCN(CC1)CC2>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19]2[NH:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:18]=2[CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 110 °C

Procedure

General Method: A mixture of 2-iodoaniline (0.315 g, 1.44 mmol), 4-oxo-1-piperidinecarboxylic acid tert-butyl ester (0.860 g, 4.31 mmol), 1,4-diazabicyclo[2.2.2]octane (Dabco™) (0.483 mL, 4.31 mmol) and palladium acetate (0.016 g, 0.072 mmol) in dry DMF (7 mL) was degassed via vacuum/argon purging, and then it was heated to 110° C. for 3.5 h. The reaction mixture was subsequently cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was separated, dried (MgSO4), filtered and evaporated to dryness. The residue was chromatographed (SiO2/hexanes:ethyl acetate, 1:1) to give the title compound (0.068 g, 17%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.88 (s, 1H), 7.45 (d, J=7.6 Hz, 1H), 7.31 (d, J=7.6 Hz, 1H), 7.12 (m, 2H), 4.64 (s, 2H), 3.82 (s, 2H), 2.82 (s, 2H), 1.50 (s, 9H); LCMS: m/e 273 (M+H)+.

Workup

customwas degassed via vacuum/argon purging
temperatureThe reaction mixture was subsequently cooled to room temperature
custompartitioned between ethyl acetate and water
customThe organic layer was separated
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated to dryness
customThe residue was chromatographed (SiO2/hexanes:ethyl acetate, 1:1)

Sources & evidence

ORD record: ord-b559cbee62c549ecaf7d135bf46b6f88
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449476B2

Reaction notes

Loading…