Potassium Phosphate, Tribasic → (4-(2-(Trifluoromethyl)pyridin-4-yl)phenyl)methanamine

HRID 711236Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.Cl.CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][NH2:28])=[CH:23][CH:22]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:9][C:8]([F:11])([F:10])[C:4]1[CH:3]=[C:2]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][NH2:28])=[CH:23][CH:22]=2)[CH:7]=[CH:6][N:5]=1

Participants

Conditions

Temperature: 96 °C

Procedure

A mixture of 4-chloro-2-(trifluoromethyl)pyridine 28-1 (54 mg, 0.3 mmol), (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine hydrochloride 28-2 (81 mg, 0.3 mmol), Pd(PPh3)4 (35 mg, 0.03 mmol) and K3PO4 (212 mg, 1.0 mmol) in dioxane (1.6 mL) and water (0.2 mL) was stirred at 96° C. under argon overnight. After cooling to room temperature, the mixture was filtered through celite (washed with ethyl acetate) and the filtrate was redistributed between ethyl acetate and water. The organic phase was dried over Na2SO4 and concentrated with rotavap. The residue was subjected to silica gel column chromatography with 7% ammonia-saturated methanol in dichloromethane as eluent to give (4-(2-(trifluoromethyl)pyridin-4-yl)phenyl)methanamine 28-3 as an oil.

Workup

temperatureAfter cooling to room temperature
filtrationthe mixture was filtered through celite (washed with ethyl acetate)
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated with rotavap

Sources & evidence

ORD record: ord-58104957f5d54efe9fda6f9ae46f75e1
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181235B2

Reaction notes

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