Cesium carbonate → HCID 90410557, compound

HRID 626579Notes

Reaction equation

HRID 626579 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:18])=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[N:19]1([C:24]([NH2:26])=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20]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.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]>[CH3:18][C:10]1[C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:26][C:24]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:25])[CH:7]=2)=[CH:14][CH:13]=[C:12]([N+:15]([O-:17])=[O:16])[N:11]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 1383351-PyrrolidinecarboxamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 904036213-((2-Chloropyridin-4-yl)oxy)-2-methyl-6-nitropyridine

Product 1

HCID 90410557HCID 90410557, compoundYield 100.3%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

A mixture of Example A3 (0.500 g, 1.882 mmol), pyrrolidine-1-carboxamide (1.074 g, 9.41 mmol), Cs2CO3 (1.226 g, 3.76 mmol) and Xantphos (0.218 g, 0.376 mmol) in dioxane (100 mL) was sparged with Ar, treated with Pd2(dba)3 (0.172 g, 0.188 mmol), sparged again with Ar and heated at 100° C. overnight. The mixture was cooled to RT, diluted with THF, the solids removed via filtration and the filtrate concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)pyrrolidine-1-carboxamide (648 mg, 100%). MS (ESI) m/z: 344.1 (M+H+).

Workup

  1. customsparged again with Ar
  2. temperatureThe mixture was cooled to RT
  3. additiondiluted with THF
  4. customthe solids removed via filtration
  5. concentrationthe filtrate concentrated to dryness
  6. custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-33a5b51066694b9e83ea4c9233753754
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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