Cesium carbonate → HCID 44553618, compound

HRID 714394Notes

Reaction equation

HRID 714394 reaction equation
[CH2:1]([NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][N:13]=[C:12](Cl)[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([CH:24]2[CH2:29][CH2:28][NH:27][C:26](=[O:30])[CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C.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].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([NH:8][C:9]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([N:27]2[CH2:28][CH2:29][CH:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:25][C:26]2=[O:30])[CH:11]=1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 15115857N-benzyl-2-chloropyridine-4-carboxamideHCID 198177874-Phenyl-2-piperidinone

Product 1

HCID 44553618HCID 44553618, compoundYield 77.8%

Reagents, catalysts & solvents 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A degassed mixture of N-benzyl-2-chloroisonicotinamide (0.05 g, 0.20 mmol), 4-phenylpiperidin-2-one (0.04 g, 0.22 mmol), cesium carbonate (0.20 g, 0.61 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.005 g, 0.008 mmol), tris(dibenzylideneacetone)dipalladium (0.004 g, 0.004 mmol) in N,N-dimethylformamide (3.0 mL) was heated at 90° C. for 18 hours and cooled to ambient temperature. The resulting solution was diluted with ethyl acetate (30 mL), washed with water (20 mL) and brine (20 mL). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give 2-oxo-4-phenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4′-carboxylic acid benzylamide as a colorless solid (0.06 g, 77%): mp 55-60° C.; 1H NMR (300 MHz, CDCl3) δ 8.46 (d, J=5.1 Hz, 1H), 8.09 (s, 1H), 7.50 (d, J=5.1 Hz, 1H), 7.40-7.16 (m, 11H), 4.59-4.46 (m, 2H), 4.09-3.84 (m, 2H), 3.24-3.09 (m, 1H), 2.79 (dd, J=17.5, 5.3 Hz, 1H), 2.61 (dd, J=17.5, 11.2 Hz, 1H), 2.26-2.22 (m, 1H), 2.13-1.95 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 170.6, 165.1, 154.8, 148.7, 143.2, 142.9, 137.8, 128.9, 128.7, 128.1, 127.6, 127.0, 126.5, 119.0, 117.8, 47.4, 44.1, 40.8, 38.6, 30.3; MS (ES+) m/z 386.5 (M+1).

Workup

  1. temperaturecooled to ambient temperature
  2. washwashed with water (20 mL) and brine (20 mL)
  3. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1372cf2f71914357939a4482a472a825
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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