Potassium Carbonate → HCID 50915499, compound

HRID 1842368Notes

Reaction equation

HRID 1842368 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:21])[CH2:12][NH:13][C:14]2[C:15](=[O:20])[NH:16][N:17]=[CH:18][CH:19]=2)[CH2:7][CH2:6]1.C([O-])([O-])=O.[K+].[K+].[F:36][C:37]([F:43])([F:42])[CH2:38][CH2:39][CH2:40]I>CN(C=O)C>[Cl:1][C:2]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:22][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:21])[CH2:12][NH:13][C:14]2[C:15](=[O:20])[N:16]([CH2:40][CH2:39][CH2:38][C:37]([F:43])([F:42])[F:36])[N:17]=[CH:18][CH:19]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27751891,1,1-Trifluoro-4-iodobutaneHCID 50915333HCID 50915333, compound

Product 1

HCID 50915499HCID 50915499, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 45 is prepared following synthesis method 6: 0.3 g (0.7 mmol) of intermediate 7b are placed in 10 mL DMF in the presence of 0.13 g (0.94 mmol) K2CO3 then 0.222 g (0.90 mmol) of 1,1,1-trifluoro-4-iodo-butane and agitated at 80° C. for 32 h. After concentrating to dryness, the residue is solubilized in water and extracted with AcOEt. The organic phases are washed in brine, dried over Na2SO4 then concentrated to dryness. The residue is purified by silica gel flash chromatography (gradient CH2Cl2-MeOH: 100:0 to 99:1 for 30 nm). 0.250 g of compound 45 are collected (yield: 67%).

Workup

  1. customsynthesis method 6
  2. concentrationAfter concentrating to dryness
  3. extractionextracted with AcOEt
  4. washThe organic phases are washed in brine
  5. dry with materialdried over Na2SO4
  6. concentrationthen concentrated to dryness
  7. customThe residue is purified by silica gel flash chromatography (gradient CH2Cl2-MeOH: 100:0 to 99:1 for 30 nm)
  8. custom0.250 g of compound 45 are collected (yield: 67%)

Sources & evidence

ORD record
ord-02f97cc921ef43fba0ccd8d3eb3a1f36
Source dataset
uspto-grants-2015_02
Patent number
US08946225B2

Reaction notes

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