Potassium Carbonate → HCID 68558982, compound

HRID 383901Notes

Reaction equation

HRID 383901 reaction equation
[CH3:1][C:2]1([CH3:34])[C:11](=[O:12])[C:10]([CH3:14])([CH3:13])[C:9]2[C:4](=[C:5]3[CH2:26][CH2:25][CH2:24][C:6]3=[C:7](B3OC(C)(C)C(C)(C)O3)[CH:8]=2)[N:3]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].Br[C:36]1[C:37]([CH:42]2[O:46][CH2:45][CH2:44][O:43]2)=[N:38][O:39][C:40]=1[CH3:41].C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C.O.C(OCC)(=O)C.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>[O:46]1[CH2:45][CH2:44][O:43][CH:42]1[C:37]1[C:36]([C:7]2[CH:8]=[C:9]3[C:4](=[C:5]4[CH2:26][CH2:25][CH2:24][C:6]=24)[N:3]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[C:2]([CH3:1])([CH3:34])[C:11](=[O:12])[C:10]3([CH3:13])[CH3:14])=[C:40]([CH3:41])[O:39][N:38]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 59233368HCID 59233368, compoundHCID 68559004HCID 68559004, compound

Product 1

HCID 68558982HCID 68558982, compoundYield 38.6%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl 2,2,4,4-tetramethyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3,4,7,8,9-hexahydro-1H-cyclopenta[h]quinolin-3-one-1-carboxylate (1.2 g) obtained in Example 1, 9) in isopropanol (11 ml) were added 4-bromo-3-[1,3]dioxolan-2-yl-5-methylisoxazole (500 mg), 2.0 M aqueous potassium carbonate solution (3.2 ml) and tetrakis(triphenylphosphine)palladium(0) (250 mg), and the mixture was stirred at 80° C. for 16 hr. The reaction solution was diluted with water and ethyl acetate, the mixture was filtered through celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to normal phase chromatography (elution solvent hexane-ethyl acetate=6:1) to give tert-butyl 6-(3-[1,3]dioxolan-2-yl-5-methylisoxazol-4-yl)-2,2,4,4-tetramethyl-2,3,4,7,8,9-hexahydro-1H-cyclopenta[h]quinolin-3-one-1-carboxylate (410 mg, 32%).

Workup

  1. filtrationthe mixture was filtered through celite
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washThe residue was subjected to normal phase chromatography (elution solvent hexane-ethyl acetate=6:1)

Sources & evidence

ORD record
ord-95e497674b5d4a77a58e33027fba3365
Source dataset
uspto-grants-2013_02
Patent number
US08367695B2

Reaction notes

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