Cesium carbonate → HCID 58237948, compound

HRID 1192926Notes

Reaction equation

HRID 1192926 reaction equation
[CH2:1]([C@:4]1([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH2:9][CH2:8][N:7]([C@H:10]([C:12]2[CH:17]=[CH:16][C:15](B3OC(C)(C)C(C)(C)O3)=[CH:14][CH:13]=2)[CH3:11])[C:6](=O)[CH2:5]1)[CH:2]=[CH2:3].Br[C:36]1[CH:37]=[CH:38][C:39](=[O:43])[N:40]([CH3:42])[CH:41]=1.C([O-])([O-])=[O:45].[Cs+].[Cs+]>O1CCOCC1.CCOC(C)=O>[CH2:1]([C@:4]1([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)[CH2:9][CH2:8][N:7]([C@H:10]([C:12]2[CH:13]=[CH:14][C:15]([C:36]3[CH:37]=[CH:38][C:39](=[O:43])[N:40]([CH3:42])[CH:41]=3)=[CH:16][CH:17]=2)[CH3:11])[C:6](=[O:45])[CH2:5]1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 130240275-Bromo-1-methylpyridin-2(1H)-oneHCID 58237926HCID 58237926, compound

Product 1

HCID 58237948HCID 58237948, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of (S)-4-allyl-4-(4-fluorophenyl)-1-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)piperidin-2-one (120 mg, 0.260 mmol), 5-bromo-1-methylpyridin-2(1H)-one (80 mg, 0.31 mmol), PdCl2(Ph3P)2 (12 mg) □ Cs2CO3 (0.4 mL, 0.8 mmol□ in 1,4-dioxane (3 mL) was heated to reflux for 2 h. The mixture was diluted with EtOAc, and washed with water. The organic phase was separated, and concentrated to give the product, which was purified by TLC to afford 5-(4-((S)-1-((S)-4-allyl-4-(4-fluorophenyl)-2-oxopiperidin-1-yl)ethyl)phenyl)-1-methylpyridin-2(1H)-one (45 mg, 39%). 1H NMR (CDCl3): δ 1.42 (t, 3H), 1.91 (m, 1H), 2.03 (m, 1H), 2.24 (m, 2H), 2.39 (m, 1H), 2.49 (d, 1H), 2.96 (m, 2H), 3.49 (s, 3H), 4.92 (m, 2H), 5.38 (m, 1H), 5.99 (m, 1H), 6.11 (m, 1H) □ 6.52 (m, 1H) □ 6.62 (m, 1H), 6.89 (m, 4H), 7.11 (m, 3H), 7.23 (m, 2H), 7.32 (m, 1H), 7.49 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. washwashed with water
  4. customThe organic phase was separated
  5. concentrationconcentrated
  6. customto give the product, which
  7. customwas purified by TLC

Sources & evidence

ORD record
ord-823429e98c7c4a60aa0f9eb7ea5eb494
Source dataset
uspto-grants-2014_03
Patent number
US08680281B2

Reaction notes

Loading…