Cesium carbonate → HCID 67083820, compound

HRID 2239524Notes

Reaction equation

HRID 2239524 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[N:8]=[N:7][C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:5]2[NH:20][C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=1[F:28].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:81][N:82]1[CH2:87][CH2:86][NH:85][CH2:84][CH2:83]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(N(C)C)=O>[CH2:13]([O:12][C:11]1[CH:10]=[C:9]2[C:4]([C:5]([NH:20][C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=3[F:28])=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:7]=[N:8]2)=[CH:3][C:2]=1[N:85]1[CH2:86][CH2:87][N:82]([CH3:81])[CH2:83][CH2:84]1)[CH3:14]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 634876Binap, (A+-)-HCID 67083816HCID 67083816, compound

Product 1

HCID 67083820HCID 67083820, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

To a 50 mL round bottom flask charged with a magnetic stir bar and ethyl 6-bromo-7-ethoxy-4-[(2-fluoro-5-methylphenyl)amino]cinnoline-3-carboxylate (0.100 g, 0.223 mmol) (Method 28) was added 2.5 mL of anhydrous dimethylacetamide. Pd2(dba)3 (50 mg, 0.55 mmol), racemic BINAP (70 mg, 0.11 mmol), cesium carbonate (150 mg, 0.45 mmol), and 1-methylpiperazine (0.334 mmol) were added to the reaction. The mixture was heated to 90° C. for 4 h before being cooled to rt and filtered though a pad of diatomaceous earth. The filtrate was concentrated in vacuo giving the crude product which was purified on 12 g silica using EtOAc/MeOH (4:1) as eluent yielding 0.033 g (32%) of the title compound as a yellow solid. m/z 468.

Workup

  1. additionTo a 50 mL round bottom flask charged with a magnetic stir bar
  2. temperaturebefore being cooled to rt
  3. filtrationfiltered though a pad of diatomaceous earth
  4. concentrationThe filtrate was concentrated in vacuo
  5. customgiving the crude product which
  6. customwas purified on 12 g silica

Sources & evidence

ORD record
ord-e3707341f34f482a9ec7c29e3f454480
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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