Sodium Carbonate → HCID 71237760, compound

HRID 1496871Notes

Reaction equation

HRID 1496871 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-b5e3004ce2fe40289a6458de0bb5bac5
Source dataset
uspto-grants-2015_12
Patent number
US09199937B2

Reaction notes

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