Triphenylphosphine → HCID 59321568, compound

HRID 2423428Notes

Reaction equation

[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:16])[C:5]=2[CH2:17][OH:18])[CH2:3][CH2:2]1.O[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[N:32]=[C:31]([C:36]([O:38][CH3:39])=[O:37])[CH:30]=[CH:29]3)=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[C:10]([Cl:16])=[CH:11][CH:12]=[CH:13][C:14]=3[Cl:15])[C:5]=2[CH2:17][O:18][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:27]=[C:28]4[C:33](=[CH:34][CH:35]=3)[N:32]=[C:31]([C:36]([O:38][CH3:39])=[O:37])[CH:30]=[CH:29]4)=[CH:24][CH:25]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of [5-cyclopropyl-3-(2,6-dichlorophenyl) -4-isoxazolyl]methanol (0.10 g, 0.36 mmol), methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate (0.10 g, 0.36 mmol) and triphenylphosphine (0.10 g, 0.39 mmol) in dichloromethane (2.5 mL) was added diisopropyl azodicarboxylate (0.071 mL, 0.39 mmol) dropwise. The solution was heated in a microwave reactor to 90° C. for 10 minutes and then allowed to sit overnight. The solution was adsorbed onto silica gel and purified by chromatography (silica gel, 0-45% ethyl acetate in hexanes gradient elution) to afford methyl 6-[4-({[5-cyclopropyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (62 mg, 32%). 1H-NMR (400 MHz, DMSO-d6) δ 8.55 (d, J=9 Hz, 1H), 8.28 (s, 1H), 8.18-8.10 (m, 3H), 7.73 (d, J=9 Hz, 2H), 7.62-7.50 (m, 3H), 6.95 (d, J=9 Hz, 2H), 4.93 (s, 2H), 3.93 (s, 3H), 2.50-2.42 (m, overlapping DMSO ˜1H), 1.20-1.12 (m, 4H). LRMS (APCI) m/z 545 (M+H)+.

Workup

custompurified by chromatography (silica gel, 0-45% ethyl acetate in hexanes gradient elution)

Sources & evidence

ORD record: ord-d481c39f29a3448a8aa6062de7d39004
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960552B2

Reaction notes

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