Cesium carbonate → HCID 123567058, compound

HRID 1918904Notes

Reaction equation

HRID 1918904 reaction equation
[F:1][C:2]1([F:14])[CH2:5][N:4]([CH2:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([NH2:13])[CH:8]=2)[CH2:3]1.Br[C:16]1[C:17](=[O:24])[N:18]([CH3:23])[CH:19]=[C:20]([Br:22])[CH:21]=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>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(Cl)Cl.C(OCC)C.CO.O1CCOCC1>[Br:22][C:20]1[CH:21]=[C:16]([NH:13][C:9]2[CH:8]=[C:7]([CH2:6][N:4]3[CH2:5][C:2]([F:1])([F:14])[CH2:3]3)[N:11]([CH3:12])[N:10]=2)[C:17](=[O:24])[N:18]([CH3:23])[CH:19]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 86661233HCID 86661233, compound

Product 1

HCID 123567058HCID 123567058, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolventHCID 22565053DCM ether MeOHSolvent

Conditions

Temperature
115 °C

Procedure

Intermediate 156g was synthesized using the same procedure as Example 112a, except using 156f (360 mg, 1.78 mmol), 3,5-dibromo-1-methyl-1H-pyridin-2-one (0.43 g, 1.6 mmol), cesium carbonate (1.56 g, 4.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.15 g, 0.16 mmol), Xantphos (0.18 g, 0.32 mmol) and 1,4-dioxane (18 mL). The reaction mixture was heated at 115° C. for 24 hours. Work-up and flash column chromatography (silica, 60:35:5 methylene chloride/diethyl ether/methanol) give 38% yield (0.23 g) of 156g as a green solid: MS (ESI+) m/z 390.1 (M+H).

Workup

  1. customIntermediate 156g was synthesized

Sources & evidence

ORD record
ord-76b5ba16228145e897d7fc6e6b5d594b
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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