Potassium Carbonate → HCID 66673554, compound

HRID 423397Notes

Reaction equation

HRID 423397 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.[C:9]([O:13][C:14](=[O:21])[NH:15][C@H:16]1[CH2:20][CH2:19][NH:18][CH2:17]1)([CH3:12])([CH3:11])[CH3:10].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:9]([O:13][C:14](=[O:21])[NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH2:17]1)([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 66673554HCID 66673554, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dissolve 5-bromo-2-fluoro-pyridine (5.20 g, 29.53 mmol), and (S)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (5.50 g, 29.53 mmol) in acetonitrile (100 mL) and reflux with K2CO3 (8.90 g, 64.96 mmol) for 3 h. Filter the reaction mixture and wash with EtOAc (100 mL). Concentrate the filtrate and purify the resulting crude material by silica gel chromatography, eluting with 40% EtOAc/hexanes to give 2.76 g (27%) of the title compound. LC-MS/ES m/z (81Br) 344.3 [M+H]+.

Workup

  1. filtrationFilter the reaction mixture
  2. washwash with EtOAc (100 mL)
  3. concentrationConcentrate the filtrate
  4. custompurify the resulting crude material by silica gel chromatography
  5. washeluting with 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-6642b0230ac648649dd04b46cf9cce6b
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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