Diisopropylamine → HCID 131728887, compound

HRID 549874Notes

Reaction equation

HRID 549874 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7](/[C:10](/[C:27]3[CH:32]=[CH:31][C:30](I)=[CH:29][CH:28]=3)=[CH:11]/[CH2:12][O:13][C:14]3[CH:25]=[CH:24][C:17]([O:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[C:16]([CH3:26])[CH:15]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[CH2:34]([N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)[C:35]#[CH:36].C(NC(C)C)(C)C>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7](/[C:10](/[C:27]3[CH:32]=[CH:31][C:30]([C:36]#[C:35][CH2:34][N:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]4)=[CH:29][CH:28]=3)=[CH:11]/[CH2:12][O:13][C:14]3[CH:25]=[CH:24][C:17]([O:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[C:16]([CH3:26])[CH:15]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 4129414-(2-Propyn-1-yl)morpholineHCID 131728886HCID 131728886, compound

Product 1

HCID 131728887HCID 131728887, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a degassed solution of the above ester (392 mg, 0.707 mmol), N-propargylmorpholine (176 mg, 1.41 mmol) and diisopropyl amine (0.466 mL, 3.3 mmol) in anhydrous tetrahydrofuran (11 mL), bis(triphenylphosphine)palladium(II) dichloride (37 mg, 0.053 mmol) and copper(I) iodide (12.0 mg, 0.063 mmol) were added. The reaction mixture was stirred at ambient temperature for 7 h under nitrogen. The solvents were evaporated in vacuo and the residue was purified by flash column chromatography (silica gel Fluka 60, chloroform/methanol 100:0-95:5) yielding methyl (Z)-[4-[3-(4-cyclopropylphenyl)-3-[4-[3-(morpholin-4-yl)propynyl]phenyl]allyloxy]-2-methylphenoxy]acetate as yellow oil.

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (silica gel Fluka 60, chloroform/methanol 100:0-95:5)

Sources & evidence

ORD record
ord-5b93e0c47729428686f8ada6e73cd909
Source dataset
uspto-grants-2011_05
Patent number
US07943613B2

Reaction notes

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