Potassium Acetate → HCID 58043878, compound

HRID 1918790Notes

Reaction equation

HRID 1918790 reaction equation
Br[C:2]1[C:3]([CH3:22])=[C:4]([N:8]2[CH2:20][CH2:19][N:11]3[C:12]4[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=4[CH:18]=[C:10]3[C:9]2=[O:21])[CH:5]=[CH:6][CH:7]=1.[O:23]1CC[O:25][BH:24]1.C([O-])(=O)C.[K+].[CH3:33][CH:34]([C:36]1[CH:41]=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)[CH:37]=1)[CH3:35]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:22][C:3]1[C:2]([B:24]2[O:25][C:34]([CH3:35])([CH3:33])[C:36]([CH3:41])([CH3:37])[O:23]2)=[CH:7][CH:6]=[CH:5][C:4]=1[N:8]1[CH2:20][CH2:19][N:11]2[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=3[CH:18]=[C:10]2[C:9]1=[O:21]

Participants

7

Reactant 4

HCID 517044Potassium AcetateHCID 5326306InChI=1/C2H5BO2/c1-2-5-3-4-1/h3H,1-2HHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 58043828Pyrazino[1,2-a]indol-1(2H)-one, 2-(3-bromo-2-methylphenyl)-3,4,6,7,8,9-hexahydro-

Product 1

HCID 58043878HCID 58043878, compoundYield 545.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

A 50-mL three-neck round-bottomed flask equipped with a reflux condenser, magnetic stirrer and nitrogen inlet was charged with of 2-(3-bromo-2-methylphenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one 101l (600 mg, 1.67 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane (1.70 g, 6.70 mmol), potassium acetate (656 mg, 6.68 mmol), and 1,4-dioxane (25 mL). After bubbling nitrogen through the resulting suspension for 30 min, XPhos (159 mg, 0.334 mmol) and tris(dibenzylideneacetone)dipalladium(0) (153 mg, 0.167 mmol) were added, and the reaction mixture was heated at 105° C. (oil bath temperature) for 14 h. After this time, the mixture was cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate (75 mL) and water (20 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3×25 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 109% crude yield (740 mg) of 2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one 101m as a yellow oil: 1H NMR (300 MHz, CDCl3) d 7.75 (dd, 1H, J=6.6, 2.1 Hz), 7.26 (m, 2H), 6.80 (s, 1H), 4.10 (m, 3H), 3.75 (m, 1H), 2.54 (m, 4H), 2.45 (s, 3H), 1.87 (m, 2H), 1.75 (m, 2H), 1.25 (s, 12H); MS (APCI+) m/z 407.7 (M+H)

Workup

  1. customA 50-mL three-neck round-bottomed flask equipped with a reflux condenser, magnetic stirrer and nitrogen inlet
  2. customAfter bubbling nitrogen through the resulting suspension for 30 min
  3. temperatureAfter this time, the mixture was cooled to room temperature
  4. filtrationfiltered
  5. additionThe filtrate was diluted with ethyl acetate (75 mL) and water (20 mL)
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with ethyl acetate (3×25 mL)
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7977cdac1c3a4f6d861a6efa1350f5ff
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

Loading…