Potassium Carbonate → Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-ethyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

HRID 17095Notes

Reaction equation

HRID 17095 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1I)[C:8](=[O:11])[O:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].O1[CH2:44][CH2:43][O:42][CH2:41]C1>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:25]1[CH:26]=[C:3]([CH2:4][CH3:5])[CH:2]=[CH:44][C:43]=1[O:42][CH3:41])[C:8](=[O:11])[O:9][CH3:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 59343876Methyl [3,5-bis(trifluoromethyl)benzyl](2-iodo-5-trifluoromethyl-benzyl)carbamate

Product 1

HCID 11699920Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-ethyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 53485975CID 53485975Catalyst

Procedure

A mixture of methyl [3,5-bis(trifluoromethyl)benzyl](2-iodo-5-trifluoromethyl-benzyl)carbamate (105 mg, 0.18 mmol) (Example 5), the title compound from Step B (58 mg, 0.22 mmol), anhydrous potassium carbonate (50 mg, 0.36 mmol), dichloro[1,1′-bis(diphenylphospino)ferrocene]palladium(II) dichloromethane adduct (14.7 mg, 0.018 mmol), and a catalytic amount of palladium acetate in anhydrous dioxane were stirred at 80° C. for approximately 40 hours. The solvent was removed in vacuo, and the title compound was obtained by preparative thin layer chromatography using 60% CH2Cl2/hexane. 1H NMR (CDCl3, 600 MHz) δ 7.71 (s, 1H), 7.56 (d, J=7.8 Hz, 1H), 7.45 (m, 2H), 7.32 (d, J=7.8 Hz, 1H), 7.25 (m, 1H), 7.21 (m, 1H), 6.88 (d, J=2.4 Hz, 1H), 6.87 (m, 1H), 4.23-4.56 (m, 4H), 3.74 (m, 3H), 3.68 (s, 3H), 2.60 (m, 2H), 1.24 (m, 3H). LC-MS (M+1) 594.0 (4.76 min).

Sources & evidence

ORD record
ord-b66bf218c54445aca1080d9bf2368514
Source dataset
uspto-grants-2010_06
Patent number
US07737295B2

Reaction notes

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