Potassium Carbonate → HCID 16768764, compound

HRID 1828692Notes

Reaction equation

Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.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:10][C:9]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([NH2:6])[CH:7]=[CH:8][C:2]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-bromo-3-(trifluoromethy)aniline (360 mg, 1.50 mmol, 1 eq.) in DMF (5 mL) is added phenyl boronic acid (274 mg, 2.25 mmol, 1.5 eq.), K2CO3 (621 mg, 4.5 mmol, 3 eq.), and tetrakis(triphenylphosphine)palladium (0) (173 mg, 0.15 mmol, 0.1 eq.). The mixture is purged with N2 (g) for 5 minutes and heated at 120° C. for 20 h. After cooling to room temperature, the reaction is diluted with EtOAc and washed with H2O followed by saturated aqueous NaCl. The organic solution is dried over Na2SO4. After concentration, the residue is purified by gradient silica gel chromatography (hexanes to 3:1 hexanes/EtOAc) to give 2-trifluoromethyl-biphenyl-4-ylamine. [MS: (ES+) 238.1 (M+1)+].

Workup

customThe mixture is purged with N2 (g) for 5 minutes
temperatureAfter cooling to room temperature
additionthe reaction is diluted with EtOAc
washwashed with H2O
dry with materialThe organic solution is dried over Na2SO4
concentrationAfter concentration
customthe residue is purified by gradient silica gel chromatography (hexanes to 3:1 hexanes/EtOAc)

Sources & evidence

ORD record: ord-70b4fdb5b5e747e78a7f3d444ed8386b
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060697B2

Reaction notes

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