Triphenylphosphine → Methyl 6-[4-({3-[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]propyl}oxy)phenyl]-2-quinolinecarboxylate

HRID 2423444Notes

Reaction equation

HRID 2423444 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.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=1[C:30]1[C:34]([CH2:35][CH2:36][CH2:37]O)=[C:33]([CH:39]([CH3:41])[CH3:40])[O:32][N:31]=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>[Cl:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([Cl:22])[C:24]=1[C:30]1[C:34]([CH2:35][CH2:36][CH2:37][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)=[C:33]([CH:39]([CH3:40])[CH3:41])[O:32][N:31]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 59321540Methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylateHCID 593215873-[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]-1-propanol

Product 1

HCID 59321559Methyl 6-[4-({3-[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]propyl}oxy)phenyl]-2-quinolinecarboxylateYield 22.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate (31 mg, 0.11 mmol), 3-[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]-1-propanol (35 mg, 0.11 mmol) and triphenylphosphine (29 mg, 0.11 mmol) in dichloromethane (1 mL) was added diisopropyl azodicarboxylate (0.020 mL, 0.11 mmol). The solution was heated in a microwave reactor at 90° C. for 10 minutes and was then adsorbed onto silica gel and purified by chromatography (silica gel, 0-35% ethyl acetate in hexanes gradient elution) to afford methyl 6-[4-({3-[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]propyl}oxy)phenyl]-2-quinolinecarboxylate (14 mg, 22%). 1H-NMR (400 MHz, CDCl3) δ 8.33 (m, 2H), 8.21 (d, J=8 Hz, 1H), 8.03-7.99 (m, 2H), 7.63 (d, J=9 Hz, 2H), 7.40-7.28 (m, 3H), 6.91 (d, J=9 Hz, 2H), 4.09 (s, 3H), 3.89 (t, J=6 Hz, 2H), 3.19 (septet, J=7 Hz, 1H), 2.51 (t, J=6 Hz, 2H), 1.82-1.76 (m, 2H), 1.33 (d, J=7 Hz, 6H).

Workup

  1. custompurified by chromatography (silica gel, 0-35% ethyl acetate in hexanes gradient elution)

Sources & evidence

ORD record
ord-3acf12f87b7c47f3bfcddc309bdc8e30
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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