Diisopropylethylamine → 4-Methyl-2-{5-[1-(4-pyrrol-1-yl-benzyl)-piperidin-3-yl]-4'-trifluoromethyl-biphenyl-3-yl}-pentanoic acid ethyl ester

HRID 889723Notes

Reaction equation

HRID 889723 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][NH:18][CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].[CH:33]([N:36]([CH:39]([CH3:41])[CH3:40])[CH2:37][CH3:38])([CH3:35])C>CC#N.CCOC(C)=O>[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][N:18]([CH2:10][C:5]3[CH:6]=[CH:40][C:39]([N:36]4[CH:33]=[CH:35][CH:38]=[CH:37]4)=[CH:41][CH:4]=3)[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 576660204-Methyl-2-(5-piperidin-3-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 576659934-Methyl-2-{5-[1-(4-pyrrol-1-yl-benzyl)-piperidin-3-yl]-4'-trifluoromethyl-biphenyl-3-yl}-pentanoic acid ethyl esterYield 185.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 33b, 4-Methyl-2-(5-piperidin-3-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (44.4 mg, 0.10 mmol) in CH3CN (5 ml) was added 1-[4-Bromomethyl) phenyl]-H-pyrrole) (35.1 mg, 0.15 mmol) and diisopropylethylamine (35 μl, 0.20 mmol). The reaction was microwaved at 150° C. for 1 hour, then continued at room temperature overnight, then diluted with EtOAc and washed with brine, sat. NaHCO3, and brine, dried and filtered. Purification by silica gel chromatography (Isco) gave the desired product, (56 mg, 94%). Calcd for C37H41F3N2O2 (M+H) 602.73, Found 603.5

Workup

  1. customThe reaction was microwaved at 150° C. for 1 hour
  2. washwashed with brine, sat. NaHCO3, and brine
  3. customdried
  4. filtrationfiltered
  5. customPurification by silica gel chromatography (Isco)

Sources & evidence

ORD record
ord-a9b426176bde4da8813b1b00119e5461
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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