Sodium Carbonate → HCID 71237760, compound

HRID 1402718Notes

Reaction equation

HRID 1402718 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[N:16]3)=[C:11]([O:19][C@@H:20]([C@H:22]3[CH2:26][NH:25][C:24](=[O:27])[CH2:23]3)[CH3:21])[CH:10]=2)O1.Br[C:30]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][N:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[F:37][C:36]([F:39])([F:38])[C:33]1[CH:34]=[CH:35][C:30]([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[N:16]3)=[C:11]([O:19][C@@H:20]([C@H:22]3[CH2:26][NH:25][C:24](=[O:27])[CH2:23]3)[CH3:21])[CH:10]=2)=[N:31][CH:32]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27364342-Bromo-5-(trifluoromethyl)pyridineHCID 71238419HCID 71238419, compound

Product 1

HCID 71237760HCID 71237760, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

500 mg (R)-4-{(R)-1-[7-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinolin-5-yloxy]-ethyl}-pyrrolidin-2-one (325 mg 2-Bromo-5-trifluoromethyl-pyridine, 46 mg Bis(triphenylphosphine)palladium(II) chloride, 1.96 mL 2N aqueous sodium carbonate and 10 mL DMF were heated at 80° C. for 18 hours. The reaction was partitioned between DCM and NaHCO3 (sat aq) then the organic layer was separated, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by MPLC using a Hept/EtOAc/MeOH gradient to give 326 mg of (R)-4-{(R)-1-[7-(5-Trifluoromethyl-pyridin-2-yl)-quinolin-5-yloxy]-ethyl}-pyrrolidin-2-one as a yellow solid.

Workup

  1. customThe reaction was partitioned between DCM and NaHCO3 (sat aq)
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by MPLC

Sources & evidence

ORD record
ord-8feb277cf8004fcbb41b0e61a9ec3b1e
Source dataset
uspto-grants-2014_12
Patent number
US08912173B2

Reaction notes

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