Cesium carbonate → HCID 86719115, compound

HRID 572936Notes

Reaction equation

HRID 572936 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.Cl.[F:14][C:15]1([F:19])[CH2:18][NH:17][CH2:16]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+]>C(Cl)Cl.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].O1CCOCC1>[F:14][C:15]1([F:19])[CH2:18][N:17]([C:2]2[N:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=2)[CH2:16]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27582473,3-Difluoroazetidine hydrochlorideHCID 53419528Methyl 2-(6-chloropyridin-3-yl)acetate

Product 1

HCID 86719115HCID 86719115, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a sealed microwave reaction vessel containing methyl 2-(6-chloropyridin-3-yl)acetate (200 mg, 1.08 mmol), 3,3-difluoroazetidine hydrochloride (154 mg, 1.19 mmol), Xantphos (93 mg, 0.162 mmol), Cs2CO3 (1.054 g, 3.23 mmol), and Pd2(dba)3 (99.0 mg, 0.11 mmol) was added 3.0 ml of dioxane. The reaction mixture was microwave radiated at 90 C for 60.0 min. It was cooled to room temperature and diluted with CH2Cl2 (20.0 ml). The suspension was filtered, washed with CH2Cl2 (3×10.0 ml), and the filtrate was washed with water and brine. The organic layer was dried over anhydrous Na2SO4, filtered. The filtrate was concentrated. The residue was purified by a standard method to give the title compound.

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with CH2Cl2 (3×10.0 ml)
  3. washthe filtrate was washed with water and brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customThe residue was purified by a standard method

Sources & evidence

ORD record
ord-048f9080076740b4bb32406085a508ae
Source dataset
uspto-grants-2015_05
Patent number
US09029531B2

Reaction notes

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