Sodium Iodide → HCID 42602841, compound

HRID 1038774Notes

Reaction equation

HRID 1038774 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[N:17]=[CH:16][C:15]([NH:18][C:19](=[O:30])[C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:14][CH:13]=3)=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:31]([N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)=[O:32].Br[CH2:40][CH:41]([CH3:43])[CH3:42].C(N(C(C)C)CC)(C)C.[I-].[Na+]>C(#N)C>[CH2:40]([N:36]1[CH2:35][CH2:34][N:33]([C:31]([C:3]2[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=2)=[CH:6][C:7]([O:11][C:12]2[N:17]=[CH:16][C:15]([NH:18][C:19](=[O:30])[C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:22][CH:21]=4)=[CH:14][CH:13]=2)=[CH:8][CH:9]=3)=[O:32])[CH2:38][CH2:37]1)[CH:41]([CH3:43])[CH3:42]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 65551-Bromo-2-methylpropaneHCID 81531DiisopropylethylamineHCID 68494150HCID 68494150, compound

Product 1

HCID 42602841HCID 42602841, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-{6-[1-methyl-2-(piperazine-1-carbonyl)-1H-indol-5-yloxy]pyridin-3-yl}-4-trifluoromethyl-benzamide (250 mg, 0.478 mmol) in acetonitrile (2 mL) were added 1-bromo-2-methylpropane (0.123 mL, 1.13 mmol), diisopropylethylamine (0.25 mL, 1.44 mmol) and sodium iodide (180 mg, 1.2 mmol). The reaction mixture was stirred under reflux for 14 hours. The solvent was removed under reduced pressure. Water was added to the residue and extracted with AcOEt. The organic layer was washed with saturated aqueous NaHCO3 and brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=40:1) and solidified with EtOH (2 mL). The precipitate was collected by filtration and dried to give 100 mg of the title compound as a white powder.

Workup

  1. temperatureunder reflux for 14 hours
  2. customThe solvent was removed under reduced pressure
  3. additionWater was added to the residue
  4. extractionextracted with AcOEt
  5. washThe organic layer was washed with saturated aqueous NaHCO3 and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography (CH2Cl2:MeOH=40:1)
  9. filtrationThe precipitate was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-66995abc35e947aca3323d3a8feda155
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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