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Triethylamine → Methyl (2s,4r)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]pyrrolidine-2-carboxylate

HRID 389193
Notes
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Reaction equation

HRID 389193 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7](=[O:14])[CH:6]=[C:5]2[O:15][C@H:16]1[CH2:20][N:19](C(OC(C)(C)C)=O)[C@H:18]([C:28]([O:30][CH3:31])=[O:29])[CH2:17]1.[CH:32]([B-](F)(F)F)=[CH2:33].[K+].CCN(CC)CC>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>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:4]([C:5]([O:15][C@H:16]3[CH2:20][NH:19][C@H:18]([C:28]([O:30][CH3:31])=[O:29])[CH2:17]3)=[CH:6][C:7](=[O:14])[NH:8]2)=[CH:3][C:2]=1[CH:32]=[CH2:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 59279885HCID 59279885, compound

Product 1

HCID 59279894Methyl (2s,4r)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]pyrrolidine-2-carboxylateYield 127.9%

Reagents, catalysts & solvents 2

HCID 178418807
HCID 178418807, compound
Catalyst
HCID 702EthanolSolvent

Procedure

To a solution of the product from Step 2 (2.26 g, 4.54 mmol) in EtOH (45.4 mL) was added potassium vinyltrifluoroborate (0.913 g, 6.82 mmol), Et3N (0.950 mL, 6.82 mmol), and PdCl2(dppf)-DCM adduct (0.186 g, 0.227 mmol). The reaction mixture was then heated to reflux for 1 hour, cooled to RT; the volatiles were evaporated in vacuo; and the residue partitioned between EtOAc and water. The organic phase 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 of the title compound. LRMS ESI+ ((M-Boc)+H)+ 345.3.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 1 hour
  3. customthe volatiles were evaporated in vacuo
  4. customand the residue partitioned between EtOAc and water
  5. dry with materialThe organic phase 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-fbe57c6449e6473b9b6e68ef195e8818
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08377874B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes