Ammonia → HCID 68185024, compound

HRID 2409965Notes

Reaction equation

HRID 2409965 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:18][C:19]3[N:24]=[C:23]([C:25]([O:27]C)=O)[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9]2)=[CH:5][CH:4]=1.[NH3:29].O1CCCC1>CO>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:18][C:19]3[N:24]=[C:23]([C:25]([NH2:29])=[O:27])[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 50903302HCID 50903302, compound

Product 1

HCID 68185024HCID 68185024, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylate (500 mg), a solution (about 7 mol/L, 20.1 mL) of ammonia in methanol, and tetrahydrofuran (6.7 mL) was stirred at room temperature for 61 hours. The reaction mixture was concentrated under reduced pressure to obtain the title compound (490 mg). 1H-NMR (CDCl3) δ ppm: 3.86 (3H, s), 4.42 (2H, s), 5.37-5.60 (1H, br), 6.77 (1H, dd, J=2.3, 8.8 Hz), 6.92 (1H, d, J=2.3 Hz), 7.24-7.29 (1H, m), 7.31-7.39 (2H, m), 7.40-7.49 (2H, m), 7.50-7.58 (2H, m), 7.69 (1H, t, J=7.8 Hz), 7.75-7.95 (1H, br), 7.97-8.03 (1H, m), 8.09 (1H, br s).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-88ddf72b5b0641a79e63df0bd9ecfd56
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

Loading…