Cesium carbonate → HCID 59300455, compound

HRID 603442Notes

Reaction equation

HRID 603442 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([CH3:9])[C:6]([OH:10])=[CH:5][CH:4]=1)[CH3:2].Br[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[C@H:21]([CH2:25][C:26]([O-:28])=[O:27])[CH2:20][CH2:19]2.[C:29](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH2:1]([C:3]1[N:8]=[C:7]([CH3:9])[C:6]([O:10][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[C@H:21]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:20][CH2:19]3)=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1706532-Methyl-6-ethyl-3-hydroxypyridineHCID 86644241HCID 86644241, compound

Product 1

HCID 59300455HCID 59300455, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6228DimethylformamideSolvent

Procedure

6-Ethyl-2-methyl-3-pyridinol (40.6 mg, 0.30 mmol) and [(1S)-5-(3-bromopropoxy)-2,3-dihydro-1H-inden-1-yl]acetate (101.0 mg, 0.30 mmol) (Example 45) were dissolved in DMF (4 mL) and cesium carbonate (193 mg, 0.59 mmol) and 4 drops of water were added. The mixture was stirred at rt for 16 h. The DMF was removed in vacuo and the residue was suspended in EtOAc and filtered. This filtrate was concentrated to give the pure title compound as a yellow oil (73 mg, 62%) which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 7.08-6.99 (m, 2H), 6.90 (d, 1H), 6.78 (s, 1H), 6.62 (dd, 1H), 4.20-4.08 (m, 4H), 3.72 (s, 3H), 3.58-3.48 (m, 1H), 2.96-2.70 (m, 6H), 2.51-2.34 (m, 4H), 2.30-2.23 (m, 2H), 1.80-1.68 (m, 1H), 1.21 (t, 3H).

Workup

  1. customThe DMF was removed in vacuo
  2. filtrationfiltered
  3. concentrationThis filtrate was concentrated

Sources & evidence

ORD record
ord-87a35d9d810d4d33943f20e584c37fc8
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

Loading…