Cesium carbonate → HCID 69080593, compound

HRID 1782040Notes

Reaction equation

HRID 1782040 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([CH2:13][CH3:14])[C:7](=[O:15])[CH:6]([C:16]([O:18][CH3:19])=[O:17])[C:5]2=[O:20].[NH2:21][C:22]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][N:23]=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+]>O.CC([O-])=O.CC([O-])=O.[Pd+2].C(#N)C.O1CCOCC1>[CH2:13]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:21][C:22]3[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:11][C:10]=2[CH3:12])[C:5](=[O:20])[CH:6]([C:16]([O:18][CH3:19])=[O:17])[C:7]1=[O:15])[CH3:14]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 153472-Amino-3-methylpyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 69082360HCID 69082360, compound

Product 1

HCID 69080593HCID 69080593, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

100 mg of methyl 6-bromo-1-ethyl-8-methyl-4-oxo-1,4-dihydroquinolone-3-carboxylate were transferred together with 40 mg of 2-amino-3-methylpyridine, 20 mg of Pd(OAc)2, 60 mg of XANTPHOS and 250 mg of cesium carbonate into a suitable reaction vessel, a protective gas atmosphere was generated with argon, and 10 ml of dioxane were added. The mixture was then heated at 80° C. for 8 h. The pure product was isolated from the reaction solution by chromatography on an HPLC system. This entailed use of a Merck Purospher RP-18 column and an acetonitrile:water mixture as eluent; the initial acetonitrile content was 15% and rose to 95% over the course of 20 minutes.

Workup

  1. additionwere added
  2. customThe pure product was isolated from the reaction solution by chromatography on an HPLC system
  3. customrose to 95% over the course of 20 minutes

Sources & evidence

ORD record
ord-1e603eb5cd654201b6b599f477ad620a
Source dataset
uspto-grants-2009_03
Patent number
US07498341B2

Reaction notes

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