Ammonium fluoride → HCID 67348256, compound

HRID 1672771Notes

Reaction equation

HRID 1672771 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N:8]2[CH2:17][C@H:16]3[N:12]([CH2:13][CH2:14][CH2:15]3)[C:11]3[N:18]=[C:19]([NH:22][CH2:23][CH3:24])[N:20]=[CH:21][C:10]=3[C:9]2=[O:25])[CH:7]=1.C([Sn](CCCC)(CCCC)[C:31]1[O:32][CH:33]=[CH:34][CH:35]=1)CCC.[F-].[NH4+]>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:23]([NH:22][C:19]1[N:20]=[CH:21][C:10]2[C:9](=[O:25])[N:8]([C:6]3[CH:7]=[C:2]([C:31]4[O:32][CH:33]=[CH:34][CH:35]=4)[CH:3]=[N:4][CH:5]=3)[CH2:17][C@H:16]3[N:12]([CH2:13][CH2:14][CH2:15]3)[C:11]=2[N:18]=1)[CH3:24]

Participants

6

Reactant 3

HCID 25516Ammonium fluorideHCID 43936882-(Tributylstannyl)furanHCID 25127532HCID 25127532, compound

Product 1

HCID 67348256HCID 67348256, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

Compound 21 (68.0 mg, 0.169 mmol) obtained in Example 21 was dissolved in toluene (4 mL), and the mixture was stirred overnight under reflux after adding tri-n-butyl(2-furyl)tin (106 mg, 0.338 mmol) and bis(triphenylphosphine)palladium dichloride (12.0 mg, 0.0169 mmol). The mixture was cooled to room temperature, vigorously stirred after adding a saturated aqueous ammonium fluoride solution, and filtered through sellite. The filtrate was collected and diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and water. The organic layer was dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was purified by preparative TLC to give the title compound (Compound 36) (40.9 mg, 62%).

Workup

  1. temperatureunder reflux
  2. stirringvigorously stirred
  3. filtrationfiltered through sellite
  4. customThe filtrate was collected
  5. additiondiluted with ethyl acetate
  6. washwashed with a saturated aqueous sodium bicarbonate solution and water
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customThe residue obtained upon concentration under reduced pressure
  9. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-f6409e9fe4534f0c9af3d4faff1beeee
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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