Cesium carbonate → HCID 59300455, compound

HRID 2235910Notes

Reaction equation

HRID 2235910 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-5eb24f9456c846e7804b982d9a726dda
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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