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

HRID 2423480Notes

Reaction equation

HRID 2423480 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[C:31]([CH2:32]O)=[C:30]([CH:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[O:29][N:28]=2)[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[C:31]([CH2:32][O:1][C:2]3[CH:7]=[CH:6][C:5]([C:8]4[CH:9]=[C:10]5[C:15](=[CH:16][CH:17]=4)[N:14]=[C:13]([C:18]([O:20][CH3:21])=[O:19])[CH:12]=[CH:11]5)=[CH:4][CH:3]=3)=[C:30]([CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)[O:29][N:28]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 59321540Methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylateHCID 59321586(3,5-Dicyclopentyl-4-isoxazolyl)methanol

Product 1

HCID 59321530Methyl 6-(4-{[(3,5-dicyclopentyl-4-isoxazolyl)methyl]oxy}phenyl)-2-quinolinecarboxylateYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate (109 mg, 0.39 mmol), (3,5-dicyclopentyl-4-isoxazolyl)methanol (92 mg, 0.39 mmol), triphenyl phosphine (102 mg, 0.39 mmol), diisopropyl azodicarboxylate (0.075 mL, 0.39 mmol) and dichloromethane (3.9 mL) were placed in a microwave reaction tube, sealed and heated in a microwave reactor to 100° C. for 10 minutes. The solution was concentrated and the residue was purified by chromatography (silica gel, hexane to 1:1 ethyl acetate:hexanes). Fractions containing the product were combined and concentrated. The residue was recrystallized from ethyl acetate and filtered to yield methyl 6-(4-{[(3,5-dicyclopentyl-4-isoxazolyl)methyl]oxy}phenyl)-2-quinolinecarboxylate (67 mg, 35%). 1H NMR (400 MHz, DMSO-d6): δ 8.57 (d, J=9 Hz, 1H), 8.33 (s, 1H), 8.19 (s, 2H), 8.12 (d, J=8 Hz, 1H), 7.84 (d, J=9 Hz, 2H), 7.17 (d, J=9 Hz, 2H), 4.98 (s, 2H), 3.94 (s, 3H), 3.41-3.37 (m, 1H), 3.16 (m, 1H), 1.98-1.94 (m, 4H), 1.76-1.56 (m, 12H).

Workup

  1. customsealed
  2. concentrationThe solution was concentrated
  3. customthe residue was purified by chromatography (silica gel, hexane to 1:1 ethyl acetate:hexanes)
  4. additionFractions containing the product
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ethyl acetate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-3b633013597f42e0bad7686781c93599
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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