Cesium carbonate → HCID 86717939, compound

HRID 1844178Notes

Reaction equation

HRID 1844178 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[CH:5]=[CH:4][N:3]=1.Br[CH2:11][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[F:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:18][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([F:19])[C:12]=1[CH2:11][O:8][C:7]1[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][C:6]=1[F:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 214366942-Amino-4-fluoropyridin-3-ol

Product 1

HCID 86717939HCID 86717939, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

55 mg (0.43 mmol) of 2-amino-4-fluoropyridin-3-ol Example 109A, 98 mg (0.47 mmol) of 2-(bromomethyl)-1,3-difluorobenzene and 308 mg (0.95 mmol) of caesium carbonate were initially charged in 1 ml of dry DMF and heated in an oil bath warmed to 50° C. for 15 min. The mixture was then filtered off and purified by preparative HPLC (Method 9). This gave 70 mg of the title compound (64% of theory).

Workup

  1. temperatureheated in an oil bath
  2. filtrationThe mixture was then filtered off
  3. custompurified by preparative HPLC (Method 9)

Sources & evidence

ORD record
ord-58b30016244d4eee9e760886516bbdaa
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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