Potassium Carbonate → (S)-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-5-cyclohexenyl-2,7-dimethylquinoline 1-oxide

HRID 931778Notes

Reaction equation

HRID 931778 reaction equation
Br[C:2]1[C:11]([C@H:12]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:23])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:25])=[N+:7]2[O-:24].[C:26]1(B(O)O)[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.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>[C:19]([O:18][C@@H:12]([C:11]1[C:2]([C:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=2)=[C:3]2[C:8](=[CH:9][C:10]=1[CH3:23])[N+:7]([O-:24])=[C:6]([CH3:25])[CH:5]=[CH:4]2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 38629021-Cyclohexenylboronic acidHCID 66631477(S)-5-bromo-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-2,7-dimethylquinoline 1-oxide2×

Product 1

HCID 66631690(S)-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-5-cyclohexenyl-2,7-dimethylquinoline 1-oxideYield 82.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

Pd(PPh3)4 (6 mg, 0.006 mmol) was added to a mixture (S)-5-bromo-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-2,7-dimethylquinoline 1-oxide (compound of Example 20) (20 mg, 0.05 mmol), cyclohexenylboronic acid (12 mg, 0.1 mmol), K2CO3 (0.09 mL 2 M in water, 0.17 mmol) in 1,2-dimethoxyethane (1 mL). The reaction mixture was flushed with nitrogen, heated at 85° C. for overnight, and then the volatile component was removed in vacuo. The residue was dissolved in ethyl acetate (30 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by HPLC to provide the desired product (17 mg, 68%). LCMS-ESI+ (m/z): 412.3 (M+H)+.

Workup

  1. customThe reaction mixture was flushed with nitrogen
  2. customthe volatile component was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (30 mL)
  4. washwashed with NaHCO3 solution, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe obtained residue was purified by HPLC

Sources & evidence

ORD record
ord-5b40d1dda43a401186fa67c46dffacc5
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

Loading…