Triphenylphosphine → HCID 18446920, compound

HRID 1268918Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[C:26](=[O:30])[CH2:25][CH2:24]2.[C:31]1([C:37]2[N:38]([CH2:61][O:62][CH2:63][CH2:64][Si:65]([CH3:68])([CH3:67])[CH3:66])[C:39]([Sn](CCCC)(CCCC)CCCC)=[C:40]([C:42]3[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=3)[N:41]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:31]1([CH:37]2[N:38]([CH2:61][O:62][CH2:63][CH2:64][Si:65]([CH3:68])([CH3:67])[CH3:66])[C:39]([C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[C:26](=[O:30])[CH2:25][CH2:24]4)=[C:40]([C:42]3[CH:43]=[CH:44][N:45]=[CH:46][CH:47]=3)[NH:41]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Palladium acetate (0.025 g, 0.11 mmol) and triphenylphosphine (0.06 g, 0.22 mmol) were suspended in toluene (1 ml). 5-bromoindanone (240 mg, 1.1 mmol) was then added and the mixture heated to 100° C. for 5 min. The solution was then treated with a solution of the product of Step 3 (0.6 g, 0.94 mmol) in toluene (1 ml) and stirred for 18 hours at 100° C. After cooling the solvent was removed in vacuo and the residue purified by silica gel chromatography, eluting with ethyl acetate to afford the title compound (0.25 g, 55%) as a yellow solid; MS(AP+) m/e 482 [M+H]+. Step 5: 5-(2-Phenyl-5-pyridin-4-yl-1H-imidazol-4-yl)-indan-1-one

Workup

temperatureAfter cooling the solvent
customwas removed in vacuo
customthe residue purified by silica gel chromatography
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-86080194b2b74540a7ab79ab16a54e52
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199137B2

Reaction notes

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