Cesium fluoride → HCID 66984307, compound

HRID 1009657Notes

Reaction equation

HRID 1009657 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8](OS(C(F)(F)F)(=O)=O)=[CH:9][CH:10]=2)[N:5]([CH:20]2[CH2:23][CH2:22][CH2:21]2)[C:4]=1[C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([O:33][CH:34]([CH:36]2[CH2:38][CH2:37]2)[CH3:35])=[O:32])=[CH:26][CH:25]=1)#[N:2].C([Sn](CCCC)(CCCC)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1)CCC.[F-].[Cs+].[F-].[K+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.CCOCC>[CH:36]1([CH:34]([O:33][C:31](=[O:32])[NH:30][C:27]2[CH:28]=[CH:29][C:24]([C:4]3[N:5]([CH:20]4[CH2:23][CH2:22][CH2:21]4)[C:6]4[C:11]([C:3]=3[C:1]#[N:2])=[CH:10][CH:9]=[C:8]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=3)[CH:7]=4)=[CH:25][CH:26]=2)[CH3:35])[CH2:37][CH2:38]1

Participants

9

Reactant 4

HCID 25953Cesium fluorideHCID 522689Potassium FluorideHCID 6077842-(Tributylstannyl)pyridineHCID 72296863HCID 72296863, compound

Product 1

HCID 66984307HCID 66984307, compoundYield 47%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of trifluoro-methanesulfonic acid 3-cyano-1-cyclobutyl-2-[4-(1-cyclopropyl-ethoxycarbonylamino)-phenyl]-1H-indol-6-yl ester prepared as in Example 1CU Step A (200 mg, 0.37 mmol) in DMF (2.0 mL) was added 2-(tributylstannyl)pyridine (160 mg, 0.44 mmol), Pd(PPh3)4 (21 mg, 0.018 mmol), CuI (7 mg, 0.037 mmol) and CsF (111 mg, 0.73 mmol). The mixture was stirred at 80° C. for 2 h, treated with ether (20 mL) and potassium fluoride (0.5 g). The mixture was stirred for another hour and filtered. The filtrate was washed with water and brine, dried over Na2SO4, concentrated and purified on silica gel (CH2Cl2/EtOAc) to provide [4-(3-cyano-1-cyclobutyl-6-pyridin-2-yl-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester as a solid (82 mg, 47%).

Workup

  1. stirringThe mixture was stirred for another hour
  2. filtrationfiltered
  3. washThe filtrate was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified on silica gel (CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-5657943658d84d53bea41ab9daadfe8a
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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