Sodium Carbonate → HCID 58641236, compound

HRID 2375461Notes

Reaction equation

HRID 2375461 reaction equation
[C:1]1([C@@H:7]2[CH:11]=[C:10](OS(C(F)(F)F)(=O)=O)[CH2:9][N:8]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].[Li+].[Cl-]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[C:10]1[CH2:9][N:8]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 2734335(2,5-Difluorophenyl)boronic acidHCID 59682332HCID 59682332, compound

Product 1

HCID 58641236HCID 58641236, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a flame dried flask equipped with stir bar was added (2S)-tert-butyl 2-phenyl-4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydro-1H-pyrrole-1-carboxylate (6-4, 0.250 g, 0.636 mmol), 2,5-difluorophenyl boronic acid (0.251 g, 1.59 mmol), Na2CO3 (0.202 g, 1.91 mmol), and LiCl (0.081 g, 1.91 mmol). The solids were dissolved in 20 mL 4:1 DME/H2O and degassed with nitrogen. Pd(PPh3)4 (0.037 g, 0.032 mmol) was added and the reaction was sealed under nitrogen and heated to 90° C. for 2 hours. Upon completion, the reaction was partitioned between 5% aq. NaHCO3 and EtOAc (3×50 mL), and the combined organic layers were dried over MgSO4. Following filtration, the organic layer was concentrated and purified via flash column chromatography (SiO2, 0-20% EtOAc/hexanes gradient) to provide (2S)-tert-butyl 4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate (6-5).

Workup

  1. customTo a flame dried flask
  2. customequipped
  3. customdegassed with nitrogen
  4. customthe reaction was sealed under nitrogen
  5. customUpon completion, the reaction was partitioned between 5% aq. NaHCO3 and EtOAc (3×50 mL)
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. filtrationfiltration
  8. concentrationthe organic layer was concentrated
  9. custompurified via flash column chromatography (SiO2, 0-20% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-e8cf62e6433744f59d2a96c8fee9c29c
Source dataset
uspto-grants-2008_12
Patent number
US07465746B2

Reaction notes

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