Cesium carbonate → HCID 66803515, compound

HRID 2366243Notes

Reaction equation

HRID 2366243 reaction equation
Br[C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[NH2:19][C:20]1[N:25]=[CH:24][N:23]=[C:22]([CH2:26][N:27]2[C:35](=[O:36])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]2=[O:37])[CH:21]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>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]>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[C:9]1[S:8][C:7]2[C:2]([NH:19][C:20]3[N:25]=[CH:24][N:23]=[C:22]([CH2:26][N:27]4[C:28](=[O:37])[C:29]5[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:35]4=[O:36])[CH:21]=3)=[N:3][CH:4]=[CH:5][C:6]=2[N:10]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 66803653HCID 66803653, compoundHCID 862804124-Bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine

Product 1

HCID 66803515HCID 66803515, compoundYield 70%

Reagents, catalysts & solvents 2

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

Procedure

To a microwave tube was added 4-bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine (100 mg, 0.280 mmol), 2-((6-aminopyrimidin-4-yl)methyl)isoindoline-1,3-dione (100 mg, 0.390 mmol), Pd2(dba)3 (32 mg, 0.035 mmol), XantPhos (30 mg, 0.052 mmol), Cs2CO3 (250 mg, 0.770 mmol) in dioxane (5.0 mL). The mixture was degassed with N2 for 10 min. The resulting mixture was irradiated in a microwave reactor at 160° C. for 2 hours and then cooled to room temperature. Insoluble solid was removed via filtration, and the residue was purified with reverse phase column chromatography eluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3 to give the desired product as a white solid (100 mg, 70% yield). LCMS: m/z: 533.1 [M+H+].

Workup

  1. customThe mixture was degassed with N2 for 10 min
  2. customThe resulting mixture was irradiated in a microwave reactor at 160° C. for 2 hours
  3. customInsoluble solid was removed via filtration
  4. customthe residue was purified with reverse phase column chromatography
  5. washeluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3

Sources & evidence

ORD record
ord-b94defb0de44470fa72845fab76259f8
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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