Cesium carbonate → 4-Methyl-2-{5-[1-(3-methyl-butyl)-piperidin-2-yl]-4'-trifluoromethyl-biphenyl-3-yl}-pentanoic acid ethyl ester

HRID 889703Notes

Reaction equation

HRID 889703 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][NH:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].I[CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37].C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][N:17]2[CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 109241-Iodo-3-methylbutaneHCID 576660784-Methyl-2-(5-piperidin-2-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 576660844-Methyl-2-{5-[1-(3-methyl-butyl)-piperidin-2-yl]-4'-trifluoromethyl-biphenyl-3-yl}-pentanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of 4-Methyl-2-(5-piperidin-2-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester, compound 10b (30.0 mg, 0.067 mmol) in CH3CN (0.5 mL) was added 1-iodo-3methylbutane (16.0 mg, 0.08 mmol) and cesium carbonate (44.0 mg, 0.134 mmol). The reaction was heated to 78° C. overnight. The reaction was cooled to room temperature, concentrated in vacuo, diluted with EtOAc, washed with NaHCO3, and brine. The solution was filtered, and concentrated, then purified via Gilson HPLC to give the compound as a light yellow oil. (31.8 mg, 92%) Calculated for C31H42F3NO2 (M+H) 517.67, Found 518.4.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additiondiluted with EtOAc
  4. washwashed with NaHCO3, and brine
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. custompurified via Gilson HPLC

Sources & evidence

ORD record
ord-0443053c97ee4b9f808688fc3750a13c
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

Loading…