Ethyl Acetate → HCID 67244304, compound

HRID 2423406Notes

Reaction equation

HRID 2423406 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([C:18]([O:20][CH3:21])=[O:19])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[CH2:23][C:24]1[C:25]([C:32]2[C:37](Cl)=[CH:36][CH:35]=[CH:34][C:33]=2[Cl:39])=[N:26][O:27][C:28]=1[CH:29]([CH3:31])[CH3:30].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C>[Cl:39][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[C:25]1[C:24]([CH2:23][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:17]=[C:16]4[C:11]([CH:12]=[C:13]([C:18]([O:20][CH3:21])=[O:19])[N:14]=[CH:15]4)=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)=[C:28]([CH:29]([CH3:31])[CH3:30])[O:27][N:26]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 592648754-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazoleHCID 59321463Methyl 7-(4-hydroxyphenyl)-3-isoquinolinecarboxylate

Product 1

HCID 67244304HCID 67244304, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 174 mg (0.62 mmol) of methyl 7-(4-hydroxyphenyl)-3-isoquinolinecarboxylate, 285 mg (0.92 mmol) of 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(1-methylethyl)isoxazole and 260 mg (1.83 mmol) of K2CO3 in 2 mL of DMF was stirred at 50° C. for 20 hr. EtOAc was added then the mixture washed with three portions of H2O, then brine. The organics were dried over Na2SO4 then evaporated and the residue purified by silica gel chromatography (40 g of silica gel eluting with 0-70% EtOAc in hexanes over 45 minutes) to give 196 mg (58%) of methyl 7-[4-({[3-(2-chlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylate as white solid. 1H NMR (400 MHz, CDCl3): δ 9.35 (s, 1H), 8.60 (s, 1H), 8.14 (s, 1H), 7.99 (m, 2H), 7.60 (d, J=9 Hz, 2H), 7.41 (d, J=9 Hz, 2H), 7.33 (m, 1H), 6.92 (d, J=9 Hz, 2H), 4.80 (s, 2H), 4.06 (s, 3H), 3.36 (septet, 1H, J=7 Hz), 1.44 (d, J=7 Hz, 6H). ESI-LCMS m/z 548 (M+H)+.

Workup

  1. washthe mixture washed with three portions of H2O
  2. dry with materialThe organics were dried over Na2SO4
  3. customthen evaporated
  4. customthe residue purified by silica gel chromatography (40 g of silica gel eluting with 0-70% EtOAc in hexanes over 45 minutes)

Sources & evidence

ORD record
ord-2d99d97d356a4028947e75e9c3e2ad34
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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