Water → HCID 56848930, compound

HRID 1470385Notes

Reaction equation

HRID 1470385 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=3)[NH2:14])[O:10][C:3]=12.[O:18]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.[Cl-].[Na+].O>[O:18]([C:25]1[CH:26]=[CH:27][C:28]([O:31][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=4)[NH2:14])[O:10][C:3]=23)=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 132544-PhenoxyphenolHCID 66779795HCID 66779795, compound

Product 1

HCID 56848930HCID 56848930, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a 10-mL microwave vial was added 3-(7-chlorofuro[3,2-b]pyridin-2-yl)aniline (88.20 mg; 0.36 mmol), 4-phenoxyphenol (100.68 mg; 0.54 mmol), and cesium carbonate (352.35 mg, 1.08 mmol). The reagents were suspended in DMF (5.00 ml) and run in the microwave reactor at 160° C. for 2 hours. The reaction mixture was cooled to room temperature. Water and brine were added to the reaction mixture which was then extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude mixture was purified using Biotage column chromatography (20-100% EtOAc/Hexanes) to afford the title compound as a white solid (111.70 mg, 79%). HPLC (method F): 91%, RT=3.949 min. MS: m/z=395 [M+H]+, RT=3.80 min.

Workup

  1. extractionwas then extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude mixture was purified

Sources & evidence

ORD record
ord-8be6b7bef5c04fedb11bb32849e019f3
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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