Cesium carbonate → HCID 66798737, compound

HRID 1193378Notes

Reaction equation

HRID 1193378 reaction equation
[CH3:1][N:2]([CH:13]1[CH2:18][CH2:17][NH:16][C:15](=[O:19])[CH2:14]1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.Br[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=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>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][N:2]([CH:13]1[CH2:18][CH2:17][N:16]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[C:15](=[O:19])[CH2:14]1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 881004-Bromopyridinium chlorideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 66799345HCID 66799345, compound

Product 1

HCID 66798737HCID 66798737, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Benzyl methyl(2-oxopiperidin-4-yl)carbamate (300 mg, 1.145 mmol, 1.0 eq.), 4-bromopyridine HCl (244 mg, 1.259 mmol, 1.1 eq.) and Cs2CO3 (744 mg, 2.29 mmol, 2.0 eq.) were taken up in toluene and degassed with N2. Xantphos (66 mg, 0.114 mmol, 0.1 eq.) and Pd2(dba)3 (104 mg, 0.114 mmol, 0.1 eq.) were then added and the mixture was heated for 14 hours at 90° C. After monitoring by TLC, the reaction mixture was filtered over Celite and the filtrate was concentrated under reduced pressure and purified by column chromatography (Alox, 1% MeOH in DCM). Yield: 41% (160 mg, 0.472 mmol)

Workup

  1. customdegassed with N2
  2. filtrationthe reaction mixture was filtered over Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. custompurified by column chromatography (Alox, 1% MeOH in DCM)

Sources & evidence

ORD record
ord-6afc62039e4c4f12bf9b0e04fcc15402
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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