Cesium carbonate → HCID 117643277, compound

HRID 2171280Notes

Reaction equation

HRID 2171280 reaction equation
[NH2:1][C:2]1(C)[CH:7]=C[CH:5]=[N:4][CH2:3]1.[C:9](=[O:12])([O-])[O-:10].[Cs+].[Cs+].C[C:16]1(C)[C:42]2[C:37](=[C:38](P(C3C=CC=CC=3)C3C=CC=CC=3)[CH:39]=[CH:40][CH:41]=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Cl[C:58]1[N:63]=[C:62]([NH:64][CH:65]2[CH2:70][CH2:69][N:68](C(OCC3C=CC=CC=3)=O)[CH2:67][CH:66]2[N:81]2[C:89](=[O:90])[C:88]3[C:83](=[CH:84][CH:85]=[CH:86][CH:87]=3)[C:82]2=[O:91])[C:61]([F:92])=[CH:60][C:59]=1[C:93]#[N:94].O1[CH2:100][CH2:99]OCC1>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]>[C:93]([C:59]1[CH:60]=[C:61]([F:92])[C:62]([NH:64][CH:65]2[CH2:70][CH2:69][N:68]([C:9]([O:10][CH2:16][C:42]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[O:12])[CH2:67][CH:66]2[N:81]2[C:82](=[O:91])[C:83]3[C:88](=[CH:87][CH:86]=[CH:85][CH:84]=3)[C:89]2=[O:90])=[N:63][C:58]=1[NH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:99]([CH3:100])[CH:7]=1)#[N:94]

Participants

7

Reactant 5

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 89174215HCID 89174215, compoundHCID 117643958HCID 117643958, compound

Product 1

HCID 117643277HCID 117643277, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

3-Amino-3-methylpyridine (9 mg), cesium carbonate (45 mg), Pd2(dba)3 (10 mg), and Xantphos (12 mg) were added to a dioxane (3 ml) solution containing benzyl 4-((6-chloro-5-cyano-3-fluoropyridin-2-yl)amino)-3-(1,3-dioxoisoindolin-2-yl)piperidin-1-carboxylate (37 mg), followed by microwave irradiation (Initiator™, 160° C., 10 minutes, 2.45 GHz, 0-240 W). The obtained residue was filtered through Celite and filter cake was washed with ethyl acetate. Subsequently, the solvent was distilled away from the filtrate under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1). Yellow oily matter of benzyl 4-((5-cyano-3-fluoro-6-((5-methylpyridin-3-yl)amino)pyridin-2-yl)amino)-3-(1,3-dioxoisoindolin-2-yl)piperidin-1-carboxylate (28 mg) was thus obtained.

Workup

  1. customfollowed by microwave irradiation (Initiator™, 160° C., 10 minutes, 2.45 GHz, 0-240 W)
  2. filtrationThe obtained residue was filtered through Celite
  3. filtrationfilter cake
  4. washwas washed with ethyl acetate
  5. distillationSubsequently, the solvent was distilled away from the filtrate under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1)

Sources & evidence

ORD record
ord-4492ee030fb946bfaf76680e36f1553c
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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