Benzene, 1-iodo-4-(trifluoromethyl)- → HCID 57666023, compound

HRID 889744Notes

Reaction equation

HRID 889744 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].I[C:34]1[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[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]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=3)[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 23676156Sodium t-butoxideHCID 576660204-Methyl-2-(5-piperidin-3-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 57666023HCID 57666023, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of compound 33b, 4-Methyl-2-(5-piperidin-3-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (35 mg, 0.08 mmol) in toluene (1.0 ml), 1-Iodo-4-trifluoromethyl-benzene (11.4 μl, 0.08 mmol), racemic-2-Ditbutylphosphino-1-1′binapthyl (14 mg, 0.035 mmol), and sodium t-butoxide ((10.0 mg, 0.01 mmol) were added and the reaction was bubbled with nitrogen for 20 minutes. The reaction was degassed with nitrogen and Pd (II) OAc) 8.0 mg, 0.01 mmol) was added. The reaction was microwaved at 120° C. for 30 minutes. The reaction was concentrated in vacuo, and purified by silica gel chromatography to give the product as a yellow oil (17 mg, 22%). Calcd for C33H35F6NO2 (M+H) 591.63, Found 592.3

Workup

  1. customthe reaction was bubbled with nitrogen for 20 minutes
  2. customThe reaction was degassed with nitrogen and Pd (II) OAc) 8.0 mg, 0.01 mmol)
  3. additionwas added
  4. customThe reaction was microwaved at 120° C. for 30 minutes
  5. concentrationThe reaction was concentrated in vacuo
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-288f42bcd5de40258545b15b8f69eef9
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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