Cesium carbonate → HCID 59186495, compound

HRID 336396Notes

Reaction equation

HRID 336396 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[N:14]=[C:15]([NH2:17])[N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.I[C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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>O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:19]4[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=4)[N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 69273Methyl 4-iodobenzoateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59186204HCID 59186204, compound

Product 1

HCID 59186495HCID 59186495, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-(3-chlorophenyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine (1.46 g, 5.97 mmol, 1 equiv), methyl 4-iodobenzoate (1.57 g, 5.99 mmol, 1.00 equiv), palladium diacetate (134 mg, 0.597 mmol, 0.100 eq), cesium carbonate (1.96 g, 6.02 mmol, 1.01 equiv), and XantPhos (173 mg, 0.299 mmol, 0.050 eq) in 1,4-dioxane was heated at 80° C. overnight. The mixture was concentrated, and the residue was diluted with methanol and water. The resulting solid was filtered and rinsed with water, isopropanol, and hexanes. The crude product was used for the next step without further purification (1.85 g, 80%). LCMS (ESI) m/z: 379.0.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with methanol and water
  3. filtrationThe resulting solid was filtered
  4. washrinsed with water, isopropanol, and hexanes
  5. customThe crude product was used for the next step without further purification (1.85 g, 80%)

Sources & evidence

ORD record
ord-518c8810af8f4057b4ae11419e928e17
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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