4-Pyridinecarboxaldehyde → (3H-Imidazol-4-ylmethyl)-(3-methoxy-phenyl)-pyridin-4-ylmethyl-amine

HRID 2043348Notes

Reaction equation

[N:1]1[CH:5]=[C:4]([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[NH:3][CH:2]=1.[N:16]1[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[N:1]1[CH:5]=[C:4]([CH2:6][N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[CH2:22][C:19]2[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=2)[NH:3][CH:2]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of (3H-imidazol-4-ylmethyl)-(3-methoxy-phenyl)-amine (0.05 g, 0.25 mmol, Example 186 step a) in 1,2-dichloroethane (2 ml) were added pyridine-4-carbaldehyde (0.06 ml, 0.64 mmol) and sodium triacetoxyborohydride (0.21 g, 0.98 mmol). The reaction mixture was stirred at 40° C. for 72 h. The reaction mixture was then concentrated in vacuo and the residue was purified using flash chromatography (column: Isolute® Flash-NH2 (Separtis); eluent: methanol/dichloromethane gradient) to yield a yellow oil (7 mg, 10%); MS (ISP): 295.3 ((M+H)+.).

Workup

concentrationThe reaction mixture was then concentrated in vacuo
customthe residue was purified

Sources & evidence

ORD record: ord-39fc9381cd2b4cd89ac8926917da483c
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586617B2

Reaction notes

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