Cesium fluoride → 1-(2-{4-[2-(3,5-Difluoro-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenoxy}-ethyl)-piperidine

HRID 1513858Notes

Reaction equation

HRID 1513858 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=1)=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[CH:6]2.[F:37][C:38]1[CH:39]=[C:40](B(O)O)[CH:41]=[C:42]([F:44])[CH:43]=1.[F-].[Cs+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:37][C:38]1[CH:39]=[C:40]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:9]=2[O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)=[CH:16][CH:15]=2)[CH:41]=[C:42]([F:44])[CH:43]=1

Participants

6

Reactant 4

HCID 25953Cesium fluorideHCID 75806TricyclohexylphosphineHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 116133766-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 575525611-(2-{4-[2-(3,5-Difluoro-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenoxy}-ethyl)-piperidineYield 101.1%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Using the procedure demonstrated in Example 9, react trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-yl ester (3.5 g, 6.67 mmol), 3,5-difluorobenzene boronic acid (3.1 g, 19.6 mmol), cesium fluoride (9.2 g, 60.4 mmol), palladium(II)acetate (145 mg, 0.64 mmol) and tricyclohexylphosphine (290 mg, 1.03 mmol) to obtain 3.3 g (100%) of the title compound: mass spectrum (ion spray) 490.3 (M+H).

Sources & evidence

ORD record
ord-7fa5e63759d84940b0ae2c862792132f
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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