Benzyl Bromide → HCID 57666027, compound

HRID 889699Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:36])[CH:5]([C:10]1[CH:11]=[C:12]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH:18]([C:22]([F:25])([F:24])[F:23])[NH:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].[CH2:37](Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CCN(C(C)C)C(C)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:36])[CH:5]([C:10]1[CH:11]=[C:12]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:31]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH:18]([C:22]([F:23])([F:24])[F:25])[N:17]2[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

4-Methyl-2-[4′-trifluoromethyl-5-(6-trifluoromethyl-piperidin-2-yl)-biphenyl-3-yl]-pentanoic acid ethyl ester, compound 7b (32 mg, 0.062 mmol), Benzyl bromide (55 μl, 0.46 mmol), DIEA (110 μl, 0.62), and tetrabutylammonium iodide (TBAI)(10 mg) in acetonitrile (0.5 mL) were combined and heated under microwave conditions 150° C. for 30 minutes. The reaction was diluted with EtOAc, washed with brine, sat. NaHCO3, and brine, dried over magnesium sulfate and filtered. Purification by silica gel chromatography gave the product as yellow oil. (56 mg, quant.) (M+H) 605.65, Found 606.2

Workup

washwashed with brine, sat. NaHCO3, and brine
dry with materialdried over magnesium sulfate
filtrationfiltered
customPurification by silica gel chromatography

Sources & evidence

ORD record: ord-e4e62442f2ab457faf815cd65e9d5fdb
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252935B2

Reaction notes

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