Cesium carbonate → HCID 90031855, compound

HRID 520793Notes

Reaction equation

HRID 520793 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][C@H:3]2[CH2:7][CH2:8][CH2:9][C@@H:2]12.F[C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][N:12]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[I:17][C:14]1[CH:15]=[CH:16][C:11]([N:1]2[C:5](=[O:6])[CH2:4][C@H:3]3[CH2:7][CH2:8][CH2:9][C@@H:2]23)=[N:12][CH:13]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27831792-Fluoro-5-iodopyridineHCID 12630591HCID 12630591, compound

Product 1

HCID 90031855HCID 90031855, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of (3aR,6aR)-hexahydrocyclopenta[b]pyrrol-2(1H)-one (210 mg, 1.68 mmol) and 2-fluoro-5-iodopyridine (412 mg, 1.85 mmol, 1.1 equiv.) in toluene (1.1 ml) were added Cs2CO3 (656 mg, 2.01 mmol, 1.2 equiv.) The reaction was stirred for 16 h at 105° C. The residue was taken up in ethyl acetate, the solids were filtered off and washed with ethyl acetate. The filtrate was concentrated in vaccuo and the residue was purified by flash chromatography (SiO2, 20 g) using a 0% to 60% ethyl acetate in heptane gradient. One obtains the title compound, (300 mg 55%), as a colorless oil, MS: m/e=329.4 (M+H+).

Workup

  1. filtrationthe solids were filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vaccuo
  4. customthe residue was purified by flash chromatography (SiO2, 20 g)

Sources & evidence

ORD record
ord-5deff13a63da4e19ab1cf37e846be798
Source dataset
uspto-grants-2016_05
Patent number
US09328090B2

Reaction notes

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