Triphenylphosphine → HCID 67244508, compound

HRID 2423440Notes

Reaction equation

HRID 2423440 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.[Cl:41][C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([Cl:48])[C:43]=1[C:49]1[C:53]([CH2:54]O)=[C:52]([C@H:56]([CH3:59])[CH2:57][CH3:58])[O:51][N:50]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[Cl:48][C:44]1[CH:45]=[CH:46][CH:47]=[C:42]([Cl:41])[C:43]=1[C:49]1[C:53]([CH2:54][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:52]([C@H:56]([CH3:59])[CH2:57][CH3:58])[O:51][N:50]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 59321540Methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylateHCID 67243941HCID 67243941, compound

Product 1

HCID 67244508HCID 67244508, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate (154 mg, 0.550 mmol), triphenylphosphine (144 mg, 0.550 mmol) and {3-(2,6-dichlorophenyl)-5-[(1R)-1-methylpropyl]-4-isoxazolyl}methanol (150 mg, 0.500 mmol) in dichloromethane (1.5 mL) was added diisopropyl azodicarboxylate (0.099 mL, 0.550 mmol) dropwise. The solution was heated in a microwave reactor at 90° C. for 10 minutes. The solution was adsorbed onto silica gel and purified by chromatography (silica gel, 0-60% ethyl acetate in hexanes gradient elution). A second purification was done by chromatography (silica gel, 1% methanol in dichloromethane) to afford methyl 6-{4-[({3-(2,6-dichlorophenyl)-5-[(1R)-1-methylpropyl]-4-isoxazolyl}methyl)oxy]phenyl}-2-quinolinecarboxylate (144 mg 0.256 mmol, 51%). 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=8 Hz, 2H), 7.63-7.51 (m, 3H), 6.92 (d, J=8 Hz, 2H), 4.88 (app q, J=12 Hz, 2H), 3.94 (s, 3H), 3.27-3.22 (m, 1H), 1.73-1.66 (m, 2H), 1.32 (d, J=7 Hz, 3H), 0.83 (t, J=7 Hz, 3H).

Workup

  1. custompurified by chromatography (silica gel, 0-60% ethyl acetate in hexanes gradient elution)
  2. customA second purification

Sources & evidence

ORD record
ord-9d23f96b91eb4992b31835edf882cba5
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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