Diisopropylethylamine → HCID 57665994, compound

HRID 889697Notes

Reaction equation

HRID 889697 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].[F:37][C:38]([F:48])([F:47])[C:39]1[CH:46]=[CH:45][C:42]([CH2:43]Br)=[CH:41][CH:40]=1.CCN(C(C)C)C(C)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[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[CH2:43][C:42]2[CH:41]=[CH:40][C:39]([C:38]([F:37])([F:47])[F:48])=[CH:46][CH:45]=2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 57665930HCID 57665930, compound

Product 1

HCID 57665994HCID 57665994, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Conditions

Temperature
150 °C

Procedure

4-Methyl-2-[4′-trifluoromethyl-5-(6-trifluoromethyl-piperidin-2-yl)-biphenyl-3-yl]-pentanoic acid ethyl ester 7b (37 mg, 0.072 mmol), 4-trifluoromethylbenzyl bromide (86 mg, 0.36 mmol), DIEA (125 μl, 0.72), and tetrabutylammonium iodide (TBAI)(10 mg, 0.096 mmol) were combined and heated under microwave conditions to 150° C. After several additions of the starting materials and ˜90 minutes under microwave, ˜50% product was formed. 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. (25 mg, 52%) (M+H) 73.65, Found 674.4

Sources & evidence

ORD record
ord-a90243b17b534e34b8cba9d89a68b835
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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