Sodium Carbonate → HCID 86682756, compound

HRID 522433Notes

Reaction equation

HRID 522433 reaction equation
Br[C:2]1[C:7]2=[N:8][N:9]3[C:18]4[CH:17]=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=4[C:12]([CH3:20])=[CH:11][C:10]3=[C:6]2[CH:5]=[C:4]([CH3:21])[CH:3]=1.CC1(C)C(C)(C)OB([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[C:33]4[CH:43]=[CH:42][CH:41]=[CH:40][C:34]4=[CH:35][CH:36]=3)[N:31]=2)O1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1.C1(C)C=CC=CC=1>[N:31]1[C:32]2[C:37](=[CH:36][CH:35]=[C:34]3[CH:40]=[CH:41][CH:42]=[CH:43][C:33]3=2)[CH:38]=[CH:39][C:30]=1[C:2]1[C:7]2=[N:8][N:9]3[C:18]4[CH:17]=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=4[C:12]([CH3:20])=[CH:11][C:10]3=[C:6]2[CH:5]=[C:4]([CH3:21])[CH:3]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 80271Tri-o-tolylphosphineHCID 66665384HCID 66665384, compoundHCID 66665403HCID 66665403, compound

Product 1

HCID 86682756HCID 86682756, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 17.0 g (50 mmol) of 10-bromo-3,5,8-trimethylindazolo[2,3-a]-quinoline (Example 86), 19.8 g (65 mmol) of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[h]quinoline, 225 mg (1 mmol) of palladium(II) acetate, 1.8 g (6 mmol) of tri-o-tolylphosphine, 10.6 g (100 mmol) of sodium carbonate, 200 ml of toluene, 50 ml of dioxane and 300 ml of water is heated under reflux for 16 h. After cooling, the organic phase is separated off, washed twice with 300 ml of water, dried over magnesium sulfate, the organic phase is evaporated to dryness in vacuo, and the residue is recrystallised from toluene/ethanol. The solid obtained in this way is freed from readily volatile and non-volatile secondary components by fractional sublimation (p about 1×10−5 mbar, T about 270° C.). Yield: 15.8 g (36 mmol), 72%, purity: about 99.5% (NMR).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. washwashed twice with 300 ml of water
  6. dry with materialdried over magnesium sulfate
  7. customthe organic phase is evaporated to dryness in vacuo
  8. customthe residue is recrystallised from toluene/ethanol
  9. customThe solid obtained in this way
  10. customby fractional sublimation (p about 1×10−5 mbar, T about 270° C.)

Sources & evidence

ORD record
ord-776a745e265a4d99810d8d606a0baad2
Source dataset
uspto-grants-2016_05
Patent number
US09331290B2

Reaction notes

Loading…