Bis(4-methoxybenzyl)amine → 2-[Bis-(4-methoxy-benzyl)-amino]-N-methoxy-N-methyl-isonicotinamide

HRID 419137Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][N:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6].[CH3:14][O:15][C:16]1[CH:32]=[CH:31][C:19]([CH2:20][NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1.CC(C)([O-])C.[Na+]>CC(C1C=CC=C(C(C)C)C=1N1C(=[Pd])N(C2C(C(C)C)=CC=CC=2C(C)C)C=C1)C.CC(C1C=CC=C(C(C)C)C=1N1C(=[Pd])N(C2C(C(C)C)=CC=CC=2C(C)C)C=C1)C.C1C=C2C(C(C=CC2=O)=O)=CC=1.C1C=C2C(C(C=CC2=O)=O)=CC=1.O1CCOCC1>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:21]([CH2:20][C:19]2[CH:31]=[CH:32][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)[C:2]2[CH:3]=[C:4]([CH:11]=[CH:12][N:13]=2)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6])=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A 40 mL vial was charged with 2-chloro-N-methoxy-N-methyl-isonicotinamide (800 mg, 3.86 mmol), bis-(4-methoxy-benzyl)-amine (1.49 g, 5.80 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene-(1,4-naphthoquinone)palladium (0) dimer (126 mg, 0.097 mmol), sodium tert-butoxide (519 mg, 5.41 mmol), and dioxane (12 mL). The vial was sealed, warmed to 110° C., and stirred overnight. The next day, the reaction was filtered through Celite, dry loaded onto silica gel, and purified via automated silica gel chromatography to generate 795 mg (47%) of the protected aminopyridine.

Workup

customThe vial was sealed
filtrationThe next day, the reaction was filtered through Celite
customdry loaded onto silica gel
custompurified

Sources & evidence

ORD record: ord-8ae75849090547a5811dcc979f85099d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093247B2

Reaction notes

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