Sodium Carbonate → 1-[4-(2-Butoxy-3,5-diisopropyl-phenyl)quinolin-6-yl]-ethanone

HRID 1394627Notes

Reaction equation

HRID 1394627 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2OS(C(F)(F)F)(=O)=O)(=[O:3])[CH3:2].[CH2:22]([O:26][C:27]1[C:32]([CH:33]([CH3:35])[CH3:34])=[CH:31][C:30]([CH:36]([CH3:38])[CH3:37])=[CH:29][C:28]=1B(O)O)[CH2:23][CH2:24][CH3:25].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:22]([O:26][C:27]1[C:32]([CH:33]([CH3:35])[CH3:34])=[CH:31][C:30]([CH:36]([CH3:37])[CH3:38])=[CH:29][C:28]=1[C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=2)[N:10]=[CH:9][CH:8]=1)[CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 17952696(2-Butoxy-3,5-diisopropylphenyl)-boronic acidHCID 59682072Trifluoro-methanesulfonic acid 6-acetyl-quinolin-4-yl ester

Product 1

HCID 596820521-[4-(2-Butoxy-3,5-diisopropyl-phenyl)quinolin-6-yl]-ethanoneYield 93%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of trifluoro-methanesulfonic acid 6-acetyl-quinolin-4-yl ester (321.7 mg, 1.008 mmol) and (2-butoxy-3,5-diisopropyl-phenyl)-boronic acid (315.3 mg, 1.133 mmol) (see Example 17, step B) in toluene (10 mL) was added 2N Na2CO3 (1.1 mL) and Pd(PPh3)4 (117.1 mg, 0.101 mmol). The solution was stirred at 80° C. for 2 h under N2 atm. The mixture was poured into brine (30 mL) and extracted with ethyl acetate (30 mL). The organic phase was dried, filtered, and concentrated. The crude material was purified by flash chromatography (2:8) ethyl acetate:hexanes to give 1-[4-(2-butoxy-3,5-diisopropyl-phenyl)quinolin-6-yl]-ethanone (378 mg, 93% yield) as a light yellow crystalline solid. Mp 132.8° C. 1H NMR (400 MHz, DMSO-d6): δ 9.01 (d, 1H, J=4.4), 8.40 (d, 1H, J=2.0), 8.25 (2d, 1H, J=2.0, 8.8), 8.16 (d, 1H, J=8.8), 7.50 (d, 1H, J=4.4), 7.24 (m, 1H), 7.00 (d, 1H, J=2.4),3.36 (m, 1H), 3.26 (m, 1H), 3.16 (m, 1H), 2.94 (m, 1H), 2.58 (s, 3H), 1.29 (m, 12H), 1.10 (m, 2H), 0.79 (m, 2H), 0.47 (t, 3H, J=7.3). 13C NMR (75 MHz, DMSO-d6): δ 197.1, 152.3, 151.6, 149.6, 147.2, 144.2, 141.6, 134.0, 129.7, 128.5, 127.2, 126.5, 125.4, 123.0, 73.0, 33.0, 31.1, 26.4, 24.0, 23.9, 23.8, 23.0, 17.9, 12.9. IR (CHCl3, cm−1): 2963, 2934, 2872, 1681. MS [EI+] 404 (M+H)+. Analytical (C27H33NO2): Calculated C, 80.36; H, 8.24; N, 3.47. Found: C, 79.98; H, 8.57; N, 3.46.

Workup

  1. extractionextracted with ethyl acetate (30 mL)
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by flash chromatography (2:8) ethyl acetate

Sources & evidence

ORD record
ord-f15559d00db0480097480f8cc3d688f8
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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