Water → HCID 68736794, compound

HRID 1878628Notes

Reaction equation

HRID 1878628 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][CH2:10]OS(C)(=O)=O)[CH:5]=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl.[F:23][C:24]1([F:29])[CH2:28][CH2:27][NH:26][CH2:25]1.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]#[C:9][CH2:10][N:26]2[CH2:27][CH2:28][C:24]([F:29])([F:23])[CH2:25]2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 249034823,3-Difluoropyrrolidine hydrochlorideHCID 86632433HCID 86632433, compound2×

Product 1

HCID 68736794HCID 68736794, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methanesulfonic acid 3-(5-bromo-pyridin-3-yl)-prop-2-ynyl ester (Intermediate 223) (1 eq, 1.95 mmol, 566 mg) in DMF (6 ml) are added K2CO3 (2.5 eq, 4.88 mmol, 674 mg) and 3,3-difluoro-pyrrolidine hydrochloride (ABCR GmbH & Co. KG, Karlsruhe, Germany) (1.2 eq, 2.34 mmol, 336 mg). The resulting mixture is heated at 80° C. for 2 h. The reaction mixture is cooled to r.t. before adding water and extracting the mixture with EtOAc. The organic layer is dried with MgSO4, filtered, and the solvents are removed in vacuo. Purification by column chromatography yields the title compound; [M+H]+=301/303.

Workup

  1. temperatureThe reaction mixture is cooled to r.t.
  2. extractionextracting the mixture with EtOAc
  3. dry with materialThe organic layer is dried with MgSO4
  4. filtrationfiltered
  5. customthe solvents are removed in vacuo
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-e5dc6f3d8546427189f31d770e0dee2c
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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