Ammonium fluoride → HCID 67351383, compound

HRID 1672758Notes

Reaction equation

HRID 1672758 reaction equation
Br[C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:31]1[O:32][CH:33]=[CH:34][N:35]=1)CCC.[F-].[NH4+]>C1(C)C=CC=CC=1.Cl[Pd-2](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:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:31]4[O:32][CH:33]=[CH:34][N:35]=4)[CH:3]=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 154861832-(Tri-n-butylstannyl)oxazoleHCID 25127213HCID 25127213, compound

Product 1

HCID 67351383HCID 67351383, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 178418903HCID 178418903, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Compound 13 (0.060 mg, 0.149 mmol) obtained in Example 13 was dissolved in toluene (3 mL), and the mixture was stirred at 100° C. for 6 hours after adding 2-(tri-n-butylstannyl)oxazole (0.062 mL, 0.298 mmol) and dichlorobis(triphenylphosphino)palladium(II) (Pd(PPh3)2Cl2; 11.0 mg, 0.0149 mmol). Thereafter, a saturated aqueous ammonium fluoride solution was added to the reaction mixture, and the mixture was vigorously stirred for 30 minutes, and filtered through sellite. After extracting the filtrate with ethyl acetate, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was purified by preparative TLC to give the title compound (Compound 15) (23.0 mg, 39%).

Workup

  1. stirringthe mixture was vigorously stirred for 30 minutes
  2. filtrationfiltered through sellite
  3. extractionAfter extracting the filtrate with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe residue obtained upon concentration under reduced pressure
  7. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-c9c61d3f8c5a4e4fb3dc597e10fc1141
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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