HCID 18753697, compound → HCID 18753706, compound

HRID 1838447Notes

Reaction equation

C(OO[CH:6]1[CH2:10][CH:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:8]=[CH:7]1)(=O)C.[K].[Cl:20][C:21]1[C:22]2[C:23]3[C:24](=[C:32]([CH3:35])[O:33][N:34]=3)[C:25](=[O:31])[NH:26][C:27]=2[CH:28]=[CH:29][CH:30]=1>CN(C=O)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Si:12]([O:11][CH:9]1[CH2:10][CH:6]([N:26]2[C:27]3[CH:28]=[CH:29][CH:30]=[C:21]([Cl:20])[C:22]=3[C:23]3=[N:34][O:33][C:32]([CH3:35])=[C:24]3[C:25]2=[O:31])[CH:7]=[CH:8]1)([C:15]([CH3:16])([CH3:17])[CH3:18])([CH3:13])[CH3:14]

Participants

Conditions

Temperature: 55 °C

Procedure

To a stirred solution of 4-(t-butyldimethylsilanyloxy)cyclopent-2-enyloxy acetate (3.4 g, 13.3 mmol) in DMF (140 mL) was added tetrakis(triphenylphosphine)palladium (1.54 g, 1.3 mmol) and 9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one potassium salt (4.4 g, 16.2 mmol). The reaction mixture was stirred at 55° C. for 6 hours. It was diluted with ethyl acetate, washed (brine), dried (Na2SO4), filtered and concentrated. Column chromatography (silica gel, hexanes/ethyl acetate, gradient) gave desired product (5.7 g, 67%). 1H NMR (CDCl3, 400 MHz) δ; 7.83 (m, 1H); 7.22 (m, 2H); 6.50 (t, 1H); 5.84 (m, 2H); 4.85 (t, 1H); 2.82 (s, 3H); 2.78 (m, 1H); 2.02 (m, 1H); 0.81 (s, 9H); 0.02 (s, 3H); 0.00 (s, 3H).

Workup

washwashed (brine)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-585026c3bf5d4c7295e63393157f7a12
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673809B2

Reaction notes

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