Oxazole, 2-(2,6-difluorophenyl)-4,5-dihydro-4-(4-iodophenyl)- → 4'-[2-(2,6-Difluorophenyl)-4,5-dihydro-4-oxazolyl][1,1'-biphenyl]-4-carbonitrile

HRID 964321Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=2)[N:13]=1.[Br-].[C:22]([C:24]1[CH:29]=[CH:28][C:27]([Zn+])=[CH:26][CH:25]=1)#[N:23]>O1CCCC1.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([C:27]3[CH:28]=[CH:29][C:24]([C:22]#[N:23])=[CH:25][CH:26]=3)=[CH:16][CH:15]=2)[N:13]=1

Participants

Conditions

Temperature: 25 °C

Procedure

The compound of Example 2 (6.5 g, 17 mmol) and bis(triphenylphosphine) palladium dichloride (0.15 g, 0.45 mmol) were dissolved in tetrahydrofuran (60 mL). The compound 4-cyanophenylzinc bromide (Rieke Organometallics, Lincoln, Nebr., 0.28M in tetrahydrofuran, 72 ml) was added over 2 min and the mixture was stirred at 25° C. for 18 h. The reaction mixture was diluted with water (200 mL) and extracted with ether (100 mL). The aqueous layer was extracted with dichloromethane (100 mL) and the combined organic layers were dried over magnesium sulfate and evaporated. The residue was subjected to silica gel chromatography with hexanes/ethyl acetate 5:1 as eluent. The title compound was isolated as a yellow solid (4.5 g): m.p. 136°-138° C. 1H NMR (CDCl3, 300 MHz) δ 7.8-7.0 (11H), 5.6 (1H), 4.9 (1H), 4.3 (1H).

Workup

extractionextracted with ether (100 mL)
extractionThe aqueous layer was extracted with dichloromethane (100 mL)
dry with materialthe combined organic layers were dried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-8a6a658b37bf46e5bf02bfd6c241669a
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05767281

Reaction notes

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