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

HRID 2423469Notes

Reaction equation

HRID 2423469 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9][CH2:10][C:11]1[C:15]([CH2:16][OH:17])=[C:14]([CH:18]([CH3:20])[CH3:19])[O:13][N:12]=1.O[C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[N:34]=[C:33]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:32]=[CH:31]3)=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>ClCCl>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[S:9][CH2:10][C:11]1[C:15]([CH2:16][O:17][C:22]2[CH:23]=[CH:24][C:25]([C:28]3[CH:29]=[C:30]4[C:35](=[CH:36][CH:37]=3)[N:34]=[C:33]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:32]=[CH:31]4)=[CH:26][CH:27]=2)=[C:14]([CH:18]([CH3:20])[CH3:19])[O:13][N:12]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 59321503[3-{[(2,6-Dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methanolHCID 59321569Ethyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate

Product 1

HCID 59321572Ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methanol (22 mg, 0.066 mmol), ethyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate (19 mg, 0.066 mmol) and triphenylphosphine (35 mg, 0.13 mmol) in dichloromethane (1 mL) was added di-tert-butyl azodicarboxylate (30 mg, 0.13 mmol). The solution was stirred at ambient temperature approximately 4.5 hours and then was adsorbed onto silica gel. Purification was done by chromatography (silica gel, 0-75% ethyl acetate in hexanes gradient elution) to afford ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (26 mg, 65%). 1H-NMR (400 MHz, CDCl3) δ 8.36-8.31 (m, 2H), 8.20 (d, J=9 Hz, 1H), 8.03-8.00 (m, 2H), 7.69 (d, J=9 Hz, 2H), 7.32-7.13 (m, 3H), 7.08 (d, J=9 Hz, 2H), 5.08 (s, 2H), 4.56 (q, J=7 Hz, 2H), 4.16 (s, 2H), 3.20 (septet, J=7 Hz, 1H), 1.49 (t, J=7 Hz, 3H), 1.31 (d, J=7 Hz, 6H). LRMS (APCI) m/z 607 (M+H)+.

Workup

  1. customPurification
  2. washwas done by chromatography (silica gel, 0-75% ethyl acetate in hexanes gradient elution)

Sources & evidence

ORD record
ord-a341cb0cc9fe4360890715d190ea8e0f
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

Loading…