HCID 67356606, compound → HCID 53378270, compound

HRID 576532Notes

Reaction equation

[CH2:1]([C:4]1([CH3:28])[C:9]2[N:10]([CH2:18][C:19]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=C)[C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][C:16]=3[C:8]=2[CH2:7][N:6]([CH3:27])[CH2:5]1)[CH:2]=C>C(Cl)Cl>[CH3:27][N:6]1[CH2:5][C:4]2([CH3:28])[CH2:1][CH:2]=[C:19]([C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)[CH2:18][N:10]3[C:9]2=[C:8]([C:16]2[CH:15]=[C:14]([CH3:17])[CH:13]=[CH:12][C:11]=23)[CH2:7]1

Participants

Conditions

Temperature: 100 °C

Procedure

4-Allyl-2,4,8-trimethyl-5-(2-pyridin-4-yl-allyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (300 mg, 0.808 mmol) was dissolved in DCM and the solution was purged with nitrogen for 5 min. Hoveyda-Grubbs 2nd generation catalyst (40 mg, 8 mol %) was added, the solution was re-purged with nitrogen and heated at 100° C. for 16 h. The reaction mixture was cooled to RT, filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by reverse phase chromatography to obtain 4 mg of 2,3a,10-trimethyl-6-pyridin-4-yl-1,2,3,3a,4,7-hexahydro-2,7a-diaza-cyclohepta[jk]fluorene. 1H NMR (Freebase, CDCl3) δ (ppm): 8.61 (d, 2H), 7.37 (m, 2H), 7.21 (s, 1H), 7.19 (d, 1H), 7.0 (d, 1H), 6.21 (m, 1H), 5.18 (d, 1H), 5.0 (d, 1H), 3.80 (d, 2H), 3.56 (d, 2H), 2.59 (s, 2H), 2.41 (s, 3H), 2.12 (s, 3H), 1.58 (s, 3H).

Workup

customthe solution was purged with nitrogen for 5 min
additionHoveyda-Grubbs 2nd generation catalyst (40 mg, 8 mol %) was added
customthe solution was re-purged with nitrogen
temperatureThe reaction mixture was cooled to RT
filtrationfiltered through Celite
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record: ord-33fce85f88974a78900952e231cd2cb3
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040519B2

Reaction notes

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