1,1,3,3-Tetramethylguanidine → HCID 86731205, compound

HRID 2277150Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](I)=[C:13]([OH:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[CH:28])=[CH:23][CH:22]=1)[CH2:18][CH3:19].CN(C)C(N(C)C)=N>CN(C=O)C.C(OCC)(=O)C.[Cu]I>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH:28]=[C:27]([C:24]3[CH:25]=[CH:26][C:21]([O:20][CH2:17][CH2:18][CH3:19])=[CH:22][CH:23]=3)[O:15][C:13]=2[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-(benzyloxy)-2-iodophenol (2.65 g), 4-propoxyphenylacetylene (1.97 g) and 1,1,3,3-tetramethylguanidine (3.08 mL) in DMF (15 mL) were added bistriphenylphosphinedichloropalladium(II) (288 mg) and copper(I) iodide (156 mg) under a nitrogen atmosphere, and the mixture was stirred at 60° C. for 30 min. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.35 g).

Workup

washwashed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-eef3e28bdb714fd7bdb722a95f33ba42
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133129B2

Reaction notes

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