Potassium Phosphate, Tribasic → N-(4-methoxybenzyl)-3-(trifluoromethyl)-[2,3'-bipyridin]-5-amine

HRID 515785Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].C(B(CC)[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:5]2[CH:4]=[C:3]([C:18]([F:21])([F:20])[F:19])[C:2]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=[N:7][CH:6]=2)=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 105 °C

Procedure

To a solution of 6-chloro-N-(4-methoxybenzyl)-5-(trifluoromethyl)pyridin-3-amine (Intermediate 1, Step 3, 1.2 g, 3.8 mmol) and 3-(diethylboryl)pyridine (0.613 g, 4.17 mmol) in 1,4-dioxane (100 mL) was added K3PO4(2.52 g, 9.48 mmol). The mixture was degassed then flushed with nitrogen before Pd2(dba)3 (173 mg, 0.02 mmol) and Xantphos (0.218 mg, 0.04 mmol) were added. The mixture was heated at 105° C. overnight. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel using EtOAc/PE=1/to afford 1 g of N-(4-methoxybenzyl)-3-(trifluoromethyl)-[2,3′-bipyridin]-5-amine.

Workup

customThe mixture was degassed
additionwere added
temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-a0a151ac70ae4112b94d11d0a92f2d41
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108944B2

Reaction notes

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