Triethylamine → 3,4,4-Trimethyl-1-(6-phenylethynyl-pyridin-3-yl)-imidazolidin-2-one

HRID 868813Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:12][C:11]([CH3:14])([CH3:13])[N:10]([CH3:15])[C:9]2=[O:16])=[CH:4][CH:3]=1.[C:17]1([C:23]#[CH:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:15][N:10]1[C:11]([CH3:14])([CH3:13])[CH2:12][N:8]([C:5]2[CH:6]=[N:7][C:2]([C:24]#[C:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:3][CH:4]=2)[C:9]1=[O:16]

Participants

Conditions

Temperature: 90 °C

Procedure

Bis-(triphenylphosphine)-palladium(II)dichloride (6 mg, 8.5 μmol, 0.03 equiv.) was dissolved in 1 ml DMF. (80 mg, 282 μmol) 1-(6-Bromo-pyridin-3-yl)-3,4,4-trimethyl-imidazolidin-2-one (E ample 3, step 2) and phenylacetylene (58 mg, 563 μmol, 2 equiv.) were added at room temperature. Triethylamine (118 μl 0.845 mmol, 3 equiv.), triphenylphosphine (4.4 mg, 16.9 μmol, 0.06 equiv.) and copper(I)iodide (1.6 mg, 8.45 μmol, 0.03 equiv.) were added and the mixture was stirred for 4 hours at 90° C. The reaction mixture was evaporated to dryness with Isolute® and the crude product was purified by flash chromatography by directly loading the solid onto a silica gel column and eluting with an ethyl acetate: heptane gradient 0:100 to 100:0. The desired 3,4,4-trimethyl-1-(6-phenylethynyl-pyridin-3-yl)-imidazolidin-2-one (52 mg, 61% yield) was obtained as a yellow solid, MS: m/e=306.2 (M+H+).

Workup

customThe reaction mixture was evaporated to dryness with Isolute®
customthe crude product was purified by flash chromatography
washeluting with an ethyl acetate

Sources & evidence

ORD record: ord-4337ace9a2374ea2ae3dc370c49af664
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969338B2

Reaction notes

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