Cesium carbonate → HCID 11518118, compound

HRID 2386936Notes

Reaction equation

HRID 2386936 reaction equation
Cl[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:29])[N:5]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:15][CH:14]=1)[C:6]([CH3:12])=[N:7]2.[C:30]1(OB(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>O1CCOCC1.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].O>[CH3:12][C:6]1[N:5]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)=[CH:17][CH:18]=2)[C:4](=[O:29])[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:7]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 78412Phenyl dihydrogen orthoborateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 11697245HCID 11697245, compound

Product 1

HCID 11518118HCID 11518118, compoundYield 18.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

5-chloro-2-methyl-3-{4-[3-(1-piperidinyl)propoxy]phenyl}-4(3H)-quinazolinone synthesized in Example 27 (100 mg, 0.24 mmol), phenylboric acid (90 mg, 0.73 mmol) and cesium carbonate (480 mg, 1.45 mmol) were mixed in 1,4-dioxane (1 mL), and the atmosphere in the system was replaced by nitrogen. Pd2(dba)3 (15 mg, 0.012 mmol) and tri-t-butylphosphine (10 mg, 0.036 mmol) were added, and stirred at 100° C. for 12 hours. Distilled water was added to the reaction mixture, and the mixture extracted with chloroform. The organic phase was washed by saturated brine, and dried with anhydrous sodium sulfate. The product was purified by thin layer silica gel chromatography, and the title compound (20 mg, 18%) was obtained as a colorless solid.

Workup

  1. extractionthe mixture extracted with chloroform
  2. washThe organic phase was washed by saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe product was purified by thin layer silica gel chromatography

Sources & evidence

ORD record
ord-27a496638dfd47a5b32274a4eb8301e6
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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