1,2-Dimethoxyethane → HCID 67111294, compound

HRID 2363164Notes

Reaction equation

HRID 2363164 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[S:20][C:21](Br)=[CH:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[CH:25]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)([CH3:27])[CH3:26].C([O-])([O-])=O.[Cs+].[Cs+].COCCOC>CCOC(C)=O.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.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[S:20][C:21]([C:32]3[CH:31]=[CH:30][CH:29]=[C:28]([CH:25]([CH3:27])[CH3:26])[CH:33]=3)=[CH:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10]

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 27734783-Isopropylbenzeneboronic acidHCID 67238529HCID 67238529, compound

Product 1

HCID 67111294HCID 67111294, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 5 ml glass tube were placed 5-bromo-thiophene-2-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (50 mg, 0.12 mmol), 3-isopropyl phenyl boronic acid (37 mg, 0.23 mmol), Cs2CO3 (114 mg, 0.34 mmol), Pd(PPh3)2Cl2 (6.4 mg, 0.009 mmol), DME (0.8 mL), ethanol (0.2 mL), and a magnetic stir bar. The vial was sealed with septum and placed into the Microwave cavity. The vial was irradiated in a Microwave synthesizer at 140° C. for 20 min. The mixture was diluted with EtOAc and washed with 1N HCl and water. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane) to give title compound (42 mg, 77%).

Workup

  1. customIn a 5 ml glass tube were placed
  2. customThe vial was sealed with septum
  3. customThe vial was irradiated in a Microwave synthesizer at 140° C. for 20 min
  4. washwashed with 1N HCl and water
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane)

Sources & evidence

ORD record
ord-ed58e750fd3d4bb286823af892ad1a67
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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