Cesium carbonate → HCID 57500382, compound

HRID 2273546Notes

Reaction equation

HRID 2273546 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:53](=[NH:66])([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.[NH2:67][C:68]1[CH:77]=[CH:76][C:75]([C:78]([C:80]2[N:84]3[CH:85]=[CH:86][CH:87]=[CH:88][C:83]3=[C:82](Br)[N:81]=2)=[O:79])=[CH:74][C:69]=1[C:70]([O:72][CH3:73])=[O:71]>CN(C)C=O.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]>[NH2:67][C:68]1[CH:77]=[CH:76][C:75]([C:78]([C:80]2[N:84]3[CH:85]=[CH:86][CH:87]=[CH:88][C:83]3=[C:82]([N:66]=[C:53]([C:60]3[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=3)[C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[N:81]=2)=[O:79])=[CH:74][C:69]=1[C:70]([O:72][CH3:73])=[O:71]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 57500383HCID 57500383, compound

Product 1

HCID 57500382HCID 57500382, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

3.83 g (11.75 mmol) of caesium carbonate, 0.73 g (1.18 mmol) of (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl [Binap], 4.93 ml (29.4 mmol) of benzophenoneimine and 0.54 mg (0.59 mmol) of tris(dibenzylideneacetone)dipalladium(0) [Pd2(dba)3] are added to the solution of 2.20 g (5.88 mmol) of methyl 2-amino-5-[(1-bromoimidazo[1,5-a]pyridin-3-yl)carbonyl]benzoate (described in Patent Application WO2006097625) in 35 ml of anhydrous N,N-dimethylformamide under argon, and the mixture is then heated at 110° C. for 3 hours. The reaction medium is then filtered and then diluted with ethyl acetate. The organic phase is washed with water and then with a saturated aqueous solution of sodium chloride. It is dried over sodium sulphate, filtered and concentrated to dryness so as to obtain a red solid. After purification by flash chromatography on silica gel (toluene/ethyl acetate/triethylamine gradient=98/1/1 to 90/9/1), 1.18 g (42%) of an orangey-red powder are obtained.

Workup

  1. filtrationThe reaction medium is then filtered
  2. additiondiluted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialIt is dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness so as
  7. customto obtain a red solid
  8. customAfter purification by flash chromatography on silica gel (toluene/ethyl acetate/triethylamine gradient=98/1/1 to 90/9/1), 1.18 g (42%) of an orangey-red powder
  9. customare obtained

Sources & evidence

ORD record
ord-31df556e96234d3a90b8dbbb0f9aa250
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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