Cesium fluoride → HCID 66705606, compound

HRID 425415Notes

Reaction equation

HRID 425415 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:10][C:9](=[O:12])[NH:8]2)=[CH:4][CH:3]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][N:22]=1.C[Sn](C)C.C[Sn](C)C.[F-].[Cs+]>O1CCOCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C:2]2[CH:19]=[CH:18][C:5]([CH2:6][C:7]3([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:10][C:9](=[O:12])[NH:8]3)=[CH:4][CH:3]=2)=[N:22][CH:23]=1

Participants

7

Reactant 4

HCID 25953Cesium fluorideHCID 27831712-Bromo-5-fluoropyridineHCID 6327618HexamethylditinHCID 59676752Ethyl 2-(4-bromobenzyl)-5-oxopyrrolidine-2-carboxylate

Product 1

HCID 66705606HCID 66705606, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Palladium tetrakis(triphenylphosphine) (213 mg, 0.18 mmol) was added to a degassed, ambient temperature solution of ethyl 2-(4-bromobenzyl)-5-oxopyrrolidine-2-carboxylate (600 mg, 1.84 mmol), 2-bromo-5-fluoropyridine (324 mg, 1.84 mmol) and hexamethylditin (603 mg, 1.84 mmol) in 1,4-dioxane (8 mL). After stirring at reflux overnight, the reaction mixture was cooled and cesium fluoride (50% on celite) was added. After stirring vigorously for 1 h, the reaction mixture was filtered and concentrated in vacuo. Chromatography over silica eluting with 40-100% ethyl acetate/hexane afforded ethyl 2-[4-(5-fluoropyridin-2-yl)benzyl]-5-oxopyrrolidine-2-carboxylate.

Workup

  1. temperatureat reflux overnight
  2. temperaturethe reaction mixture was cooled
  3. stirringAfter stirring vigorously for 1 h
  4. filtrationthe reaction mixture was filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-136d15af5bc74ea3aadde12adf048de3
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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