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

HRID 2423433Notes

Reaction equation

HRID 2423433 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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:41]1([C:44]2[O:48][N:47]=[C:46]([C:49]3[C:54]([Cl:55])=[CH:53][N:52]=[CH:51][C:50]=3[Cl:56])[C:45]=2[CH2:57]O)[CH2:43][CH2:42]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[CH:41]1([C:44]2[O:48][N:47]=[C:46]([C:49]3[C:50]([Cl:56])=[CH:51][N:52]=[CH:53][C:54]=3[Cl:55])[C:45]=2[CH2:57][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)[CH2:43][CH2:42]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 593215255-Cyclopropyl-3-(3,5-dichloro-4-pyridyl)isoxazole-4-methanolHCID 59321540Methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate

Product 1

HCID 59321467Methyl 6-[4-({[5-cyclopropyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylateYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate (81 mg, 0.29 mmol), triphenylphosphine (84 mg, 0.32 mmol) and [5-cyclopropyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methanol (83 mg, 0.29 mmol) in dichloromethane (2.5 mL) was added diisopropyl azodicarboxylate (0.058 mL, 0.32 mmol) dropwise. The solution was heated in a microwave reactor at 90° C. for 10 minutes and then allowed to stand overnight. The solution was adsorbed onto silica gel and purified by chromatography (silica gel, 0-1.25% methanol in chloroform gradient elution) to afford methyl 6-[4-({[5-cyclopropyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (70 mg, 44%). 1H-NMR (400 MHz, CDCl3) δ 8.60 (s, 2H), 8.39-8.33 (m, 2H), 8.22 (d, J=9 Hz, 1H), 8.01-7.96 (m, 2H), 7.60 (d, J=9 Hz, 2H), 6.88 (d, J=9 Hz, 2H), 4.90 (s, 2H), 4.09 (s, 3H), 2.22-2.15 (m, 1H), 1.33-1.13 (m, 4H).

Workup

  1. custompurified by chromatography (silica gel, 0-1.25% methanol in chloroform gradient elution)

Sources & evidence

ORD record
ord-6398ff52e0d744ba9bb86c093bd94835
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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