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 2293027Notes

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., 0.28 M 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-1a717bbe34c840c3ade02ae42c125963
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686393

Reaction notes

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