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Potassium vinyltrifluoroborate → 1-tert-butyl 2-methyl (2S,4R)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

HRID 2045708
Notes
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Reaction equation

HRID 2045708 reaction equation
[CH:1]([B-](F)(F)F)=[CH2:2].[K+].Br[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[NH:15][C:14](=[O:21])[CH:13]=[C:12]2[O:22][C@H:23]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:25]([C:35]([O:37][CH3:38])=[O:36])[CH2:24]1>CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:20][O:19][C:18]1[CH:17]=[C:16]2[C:11]([C:12]([O:22][C@H:23]3[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:25]([C:35]([O:37][CH3:38])=[O:36])[CH2:24]3)=[CH:13][C:14](=[O:21])[NH:15]2)=[CH:10][C:9]=1[CH:1]=[CH2:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 59279885HCID 59279885, compound

Product 1

HCID 592799081-tert-butyl 2-methyl (2S,4R)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylateYield 99.1%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalyst
HCID 702
Ethanol
Solvent

Procedure

Potassium vinyltrifluoroborate (0.913 g, 6.82 mmol), TEA (0.950 mL, 6.82 mmol), and PdCl2(dppf)-CH2Cl2 adduct (0.186 g, 0.227 mmol) were added to a solution of the product from step 2 (2.26 g, 4.54 mmol) in EtOH (45.4 mL). The mixture was then heated to reflux for 1 h. The EtOH was removed in vacuo, and the residue was taken up in EtOAc and extracted with water. The organic layer was dried over MgSO4, and the solvent was removed in vacuo. The crude material was purified on silica gradient elution, 0-5% MeOH/DCM) to yield 2.0 g (99%) of the title compound. LRMS ESI+ ((M-Boc)+H)+345.3.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 1 h
  3. customThe EtOH was removed in vacuo
  4. extractionextracted with water
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent was removed in vacuo
  7. customThe crude material was purified on silica gradient elution, 0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-f93848d647e94569bf633da037048bff
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08591878B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes