Cesium carbonate → HCID 67194489, compound

HRID 1259361Notes

Reaction equation

HRID 1259361 reaction equation
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+].[CH2:53]([N:60]1[C:64]2=[C:65]([N+:79]([O-:81])=[O:80])[C:66](OS(C(F)(F)F)(=O)=O)=[C:67]([CH3:70])[C:68](=[O:69])[N:63]2[CH2:62][CH2:61]1)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.[Br:82][C:83]1[CH:88]=[CH:87][C:86]([NH2:89])=[C:85]([F:90])[CH:84]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:53]([N:60]1[C:64]2=[C:65]([N+:79]([O-:81])=[O:80])[C:66]([NH:89][C:86]3[CH:87]=[CH:88][C:83]([Br:82])=[CH:84][C:85]=3[F:90])=[C:67]([CH3:70])[C:68](=[O:69])[N:63]2[CH2:62][CH2:61]1)[C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 1230504-Bromo-2-fluoroanilineHCID 634876Binap, (A+-)-HCID 58380548HCID 58380548, compound

Product 1

HCID 67194489HCID 67194489, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

Palladium acetate (129 mg, 0.001 mol), BINAP (538 mg, 0.001 mol), cesium carbonate (2.8 g, 0.009 mol) were dissolved in toluene (20 mL) and the resulting mixture was sparged for 30 mins with nitrogen. This was followed by addition of trifluoro-methanesulfonic acid 1-benzyl-6-methyl-8-nitro-5-oxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyridin-7-yl ester (2.5 g, 0.006 mol) and 4-bromo-2-fluoro-phenylamine (1.15 g, 0.006 mol) in toluene (20 mL) and the reaction flask was again sparged for another 15 minutes. The reaction mixture was heated at 90° C. for 1 hour. The reaction was monitored by TLC (80% ethylacetate in hexane). The reaction mixture was filtered through celite bed and concentrated. Purification by column chromatography on silica gel (40% ethylacetate in hexane) afforded 1.3 g of the product (48% yield).

Workup

  1. customthe resulting mixture was sparged for 30 mins with nitrogen
  2. customthe reaction flask was again sparged for another 15 minutes
  3. filtrationThe reaction mixture was filtered through celite bed
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (40% ethylacetate in hexane)

Sources & evidence

ORD record
ord-dffd0f3ac9264a568942bd134deb4178
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

Loading…