Diisopropylamine → HCID 86629277, compound

HRID 1810622Notes

Reaction equation

HRID 1810622 reaction equation
C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C1CCCCC1.Br[C:21]1[CH:26]=[CH:25][C:24](/[C:27](/[C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=2)=[CH:28]/[CH2:29][O:30][C:31]2[CH:42]=[CH:41][C:34]([O:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[C:33]([CH3:43])[CH:32]=2)=[CH:23][CH:22]=1.[C:51]([C:53]1[CH:58]=[CH:57][C:56]([CH3:59])=[CH:55][CH:54]=1)#[CH:52].C(NC(C)C)(C)C>O1CCCC1.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.[Cu]I>[Cl:50][C:47]1[CH:48]=[CH:49][C:44](/[C:27](/[C:24]2[CH:25]=[CH:26][C:21]([C:52]#[C:51][C:53]3[CH:58]=[CH:57][C:56]([CH3:59])=[CH:55][CH:54]=3)=[CH:22][CH:23]=2)=[CH:28]\[CH2:29][O:30][C:31]2[CH:42]=[CH:41][C:34]([O:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[C:33]([CH3:43])[CH:32]=2)=[CH:45][CH:46]=1

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 8078CyclohexaneHCID 13018p-EthynyltolueneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 86629278HCID 86629278, compound

Product 1

HCID 86629277HCID 86629277, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

In nitrogen atmosphere, bis(benzonitrile)palladium(II) chloride (14.6 mg, 0.038 mmol), copper(I) iodide (12.1 mg, 0.064 mmol) and 0.15 M solution of tri(tert-butyl)phosphine in cyclohexane (0.60 mL, 0.090 mmol) were added to a degassed solution of methyl (E)-[4-[3-(4-bromophenyl)-3-(4-chlorophenyl)allyloxy]-2-methylphenoxy]acetate (383 mg, 0.763 mmol), 4-ethynyltoluene (115 mg, 0.990 mmol) and diisopropyl amine (0.50 mL, 3.57 mmol) in dry tetrahydrofuran (6 mL). In atmosphere of nitrogen, the reaction mixture was stirred at 60° C. for 4 h, cooled down and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 12:1) yielding methyl (Z)-[4-[3-(4-chlorophenyl)-3-[4-(4-methylphenylethynyl)phenyl]allyloxy]-2-methylphenoxy]acetate as brownish oil.

Workup

  1. temperaturecooled down
  2. customevaporated in vacuo
  3. customThe residue was purified by flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 12:1)

Sources & evidence

ORD record
ord-112ed297e9354c2a956aaa9782e11de5
Source dataset
uspto-grants-2013_01
Patent number
US08362016B2

Reaction notes

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