1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86703275, compound

HRID 2409953Notes

Reaction equation

HRID 2409953 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[NH:7][C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:5]2.[CH:19]([C:21]1[N:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:23][CH:22]=1)=[O:20].C1CCN2C(=NCCC2)CC1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[NH:7][C:6]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[C:5]2[CH:19]([OH:20])[C:21]1[N:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 12575850Methyl 6-formylpyridine-2-carboxylateHCID 69096927HCID 69096927, compound

Product 1

HCID 86703275HCID 86703275, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-fluoro-6-methoxy-2-phenyl-1H-indole (176 mg) and methyl 6-formylpyridine-2-carboxylate (133 mg) in dichloromethane (3.6 mL) was added 1,8-diazabicyclo[5,4,0]-7-undecene (0.011 mL), and this mixture was stirred at room temperature for 20 hours. The reaction mixture was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (210 mg). 1H-NMR (CDCl3) δ ppm: 3.88 (3H, s), 4.05 (3H, s), 5.31 (1H, d, J=2.8 Hz), 6.10-6.16 (1H, m), 6.81 (1H, d, J=11.8 Hz), 6.91 (1H, d, J=7.0 Hz), 7.23-7.29 (1H, m), 7.38-7.54 (3H, m), 7.66-7.75 (3H, m), 8.00-8.06 (1H, m), 8.12 (1H, br s).

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-febdea0661fb4948b57282d6380c3470
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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