Phenylacetylene → HCID 12018748, compound

HRID 1860691Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:5]=[CH:4][C:3]=1[CH2:19][C:20]([CH3:28])([CH3:27])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:48]1([C:54]#[CH:55])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CCN(CC)CC.C(OCC)(=O)C.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>[CH3:27][C:20]([CH3:28])([CH2:19][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:7][C:2]=1[C:55]#[C:54][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 4-{2-bromo-4-[3-(pyridin-2-ylamino)propoxy]phenyl}-3,3-dimethylbutanoate (500 mg) was dissolved in Et3N (5 ml) followed by the addition of phenylylacetylene (250 μL), Cul (11 mg), triphenylphosphine (85 mg), and Pd(Ph3P)2Cl2 (42 mg). The reaction mixture was heated to 80° C. under a nitrogen atmosphere for 24 hours. Further phenylacetylene (125 μL) and triethylamine (5 mL) were added and heating was continued for a further 24 h. The mixture was cooled to room temperature, diluted with ethyl acetate (50 mL) and filtered through a pad of celite. The solvent was evaporated and the residue was chromatographed on silica gel eluting with hexane/ethyl acetate (3:2). This gave the product (516 mg) as an oil. The NMR spectrum was consistent for the proposed structure.

Workup

temperatureheating
temperatureThe mixture was cooled to room temperature
filtrationfiltered through a pad of celite
customThe solvent was evaporated
customthe residue was chromatographed on silica gel eluting with hexane/ethyl acetate (3:2)

Sources & evidence

ORD record: ord-b53f4be844474367a543861c2d2a5ea7
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531494B1

Reaction notes

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