3-Pyridinecarboxaldehyde → HCID 44467088, compound

HRID 1642424Notes

Reaction equation

HRID 1642424 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:19][CH:18]=[CH:17][N:5]2[C:6](=[O:16])[C:7]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=1.[O-]CC.[Na+]>C(O)C>[O:16]=[C:6]1[N:5]2[CH:17]=[CH:18][S:19][C:4]2=[N:3][C:2](/[CH:1]=[CH:20]/[C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[C:7]1[C:8]1[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 2723922Sodium ethoxideHCID 66752927HCID 66752927, compound

Product 1

HCID 44467088HCID 44467088, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared by condensation of Intermediate 4 (350 mg, 1.309 mmol) with nicotinaldehyde (196 mg, 1.833 mmol) in presence of sodium ethoxide (178 mg, 2.618 mmol) in ethanol (15 ml) according to the procedure outlined in Example 9 to give 266 mg of the desired product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 6.88 (d, J=15.6 Hz, 1H), 7.30-7.38 (m, 1H), 7.50-7.58 (m, 3H), 7.84-7.93 (m, 4H), 8.02 (d, J=4.8 Hz, 1H), 8.47 (d, J=3.9 Hz, 1H), 8.70 (s, 1H); ESI-MS (m/z) 357.32 (M+H)+.

Sources & evidence

ORD record
ord-2ae08b23da274d5f94fbd34d4eac0f8f
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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