Dichloromethane → N-(4-tert-butylphenyl)-4-(3-isoxazolyl)benzamide

HRID 736396Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:20]([C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)([CH3:23])([CH3:22])[CH3:21].C(Cl)Cl.[O:34]1CCC[CH2:35]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:20]([C:24]1[CH:25]=[CH:26][C:27]([NH:28][C:35](=[O:34])[C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:12]=[CH:11][O:10][N:9]=3)=[CH:4][CH:3]=2)=[CH:29][CH:30]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

Conditions

Temperature: 120 °C

Procedure

The product from Example 42C (56.1 mg, 0.250 mmol), triethylamine (55 μL, 0.39 mmol), 4-tert-butylaniline (52 μL, 0.33 mmol), and Pd(dppf)Cl2:CH2Cl2 (20.4 mg, 0.025 mmol) were combined in tetrahydrofuran (10 mL) and heated at 120° C. under a carbon monoxide atmosphere (700 psi) for 16 hours. The mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was purified by flash chromatography (20% ethyl acetate in hexanes) to provide the title compound as a solid. 1H NMR (300 MHz, CDCl3) δ 8.51 (d, 1H), 7.96 (s, 4H), 7.82 (br s, 1H), 7.57 (d, 2H), 7.41 (d, 2H), 6.73 (d, 1H), 1.33 (s, 9H); MS (m/z) 321.

Workup

temperatureto cool to room temperature
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-b07e3bc4d4964134b7b4199e63a8915a
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595332B2

Reaction notes

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