1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86703322, compound

HRID 2410007Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]3[CH:13]=[N:14][CH:15]=[N:16][CH:17]=3)[NH:9]2)=[CH:5][CH:4]=1.[CH:18]([C:20]1[N:25]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=[CH:22][CH:21]=1)=[O:19].C1CCN2C(=NCCC2)CC1>ClCCl>[OH:19][CH:18]([C:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[NH:9][C:8]=1[C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1)[C:20]1[N:25]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a suspension of 6-methoxy-2-pyrimidin-5-yl-1H-indole (779 mg) and methyl 6-formylpyridine-2-carboxylate (628 mg) in dichloromethane (17.3 mL) was added 1,8-diazabicyclo[5,4,0]-7-undecene (0.052 mL), and the mixture was stirred at 30° C. for 76 hours. The reaction mixture was purified by aminopropylated silica gel column chromatography (eluting solvent: methanol-ethyl acetate) to obtain the title compound (829 mg). 1H-NMR (DMSO-d6) δ ppm: 3.75 (3H, s), 3.82 (3H, s), 5.99 (1H, d, J=3.5 Hz), 6.16 (1H, d, J=3.5 Hz), 6.61 (1H, dd, J=2.3, 8.8 Hz), 6.84 (1H, d, J=2.3 Hz), 7.49 (1H, d, J=8.8 Hz), 7.86-7.92 (1H, m), 8.06 (1H, t, J=7.8 Hz), 8.18-8.26 (1H, m), 9.23 (1H, s), 9.55 (2H, s), 11.40 (1H, br s).

Workup

customThe reaction mixture was purified by aminopropylated silica gel column chromatography (eluting solvent: methanol-ethyl acetate)

Sources & evidence

ORD record: ord-23a280de98df4d58902212f445f7d137
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815903B2

Reaction notes

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