Triphenylphosphine → Methyl 6-[4-({[5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

HRID 2423410Notes

Reaction equation

HRID 2423410 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]=[C:13]([C:18]([O:20][CH3:21])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1.[CH:22]1([C:27]2[O:31][N:30]=[C:29]([C:32]3[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:39])[C:28]=2[CH2:40]O)[CH2:26][CH2:25][CH2:24][CH2:23]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:22]1([C:27]2[O:31][N:30]=[C:29]([C:32]3[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:39])[C:28]=2[CH2:40][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]=[C:10]4[C:15](=[CH:16][CH:17]=3)[N:14]=[C:13]([C:18]([O:20][CH3:21])=[O:19])[CH:12]=[CH:11]4)=[CH:4][CH:3]=2)[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 59321540Methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylateHCID 59709035[5-Cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methanol

Product 1

HCID 59321578Methyl 6-[4-({[5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylateYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate (0.10 mg, 0.36 mmol), [5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methanol (0.11 mg, 0.36 mmol) and triphenylphosphine (0.10 mg, 0.39 mmol) in dichloromethane (2.5 mL) was added diisopropyl azodicarboxylate (0.071 mL, 0.39 mmol) slowly. The solution was heated in a microwave reactor at 90° C. for 10 minutes and then 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-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (76 mg, 37%). 1H-NMR (400 MHz, DMSO d6) δ 8.55 (d, J=8 Hz, 1H), 8.28 (s, 1H), 8.18-8.10 (m, 3H), 7.73 (d, J=9 Hz, 2H), 7.63-7.51 (m, 3H), 6.96 (d, J=9 Hz, 2H), 4.98 (s, 2H), 3.93 (s, 3H), 3.58-3.50 (m, 1H), 2.11-2.03 (m, 2H), 1.84-1.64 (m, 6H).

Workup

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

Sources & evidence

ORD record
ord-0a0e531e9634483385905449498560bc
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

Loading…