Ammonium Chloride → HCID 86688546, compound

HRID 710549Notes

Reaction equation

HRID 710549 reaction equation
Br[C:2]1[CH:26]=[CH:25][C:5]2[N:6]=[C:7]([NH:9][C:10]([N:12]3[CH2:17][CH2:16][C:15](=[CH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[CH2:14][CH2:13]3)=[O:11])[S:8][C:4]=2[CH:3]=1.[CH3:27][C:28]1[C:32](B2OC(C)(C)C(C)(C)O2)=[C:31]([CH3:42])[O:30][N:29]=1.CC(C)([O-])C.[Na+].[Cl-].[NH4+]>C(COC)OC.O.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>[CH3:27][C:28]1[C:32]([C:2]2[CH:26]=[CH:25][C:5]3[N:6]=[C:7]([NH:9][C:10]([N:12]4[CH2:17][CH2:16][C:15](=[CH:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=5)[CH2:14][CH2:13]4)=[O:11])[S:8][C:4]=3[CH:3]=2)=[C:31]([CH3:42])[O:30][N:29]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 27586563,5-Dimethylisoxazole-4-boronic acid pinacol esterHCID 23676156Sodium t-butoxideHCID 86688544HCID 86688544, compound

Product 1

HCID 86688546HCID 86688546, compoundYield 88.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

The compound (300 mg, 699 μmol) obtained in Example 1 and 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)isoxazole (458 mg, 2.10 mmol) were dissolved in a mixture of dimethoxyethane (10 mL) and water (1 mL), under a nitrogen atmosphere, sodium tert-butoxide (470 mg, 4.9 mmol) and tetrakis(triphenylphosphine)palladium(0) (323 mg, 280 μmol) were added thereto, followed by stirring for 16 hours while heating under reflux. A saturated ammonium chloride aqueous solution was added to the resulting mixture to stop the reaction, and after extraction with ethyl acetate, the extract was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The desiccant was filtered off, and the residue obtained by evaporation under reduced pressure was purified using medium pressure flash column chromatography (silica gel; methanol:chloroform=1:100), thereby giving the title compound (275 mg, 88%) as an amorphous solid.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. customthe reaction
  4. extractionafter extraction with ethyl acetate
  5. washthe extract was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe desiccant was filtered off
  8. customthe residue obtained by evaporation under reduced pressure
  9. customwas purified

Sources & evidence

ORD record
ord-a039e006def8471ab1e926407bc7871d
Source dataset
uspto-grants-2015_11
Patent number
US09181183B2

Reaction notes

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