1,2-Dimethoxyethane → HCID 67111294, 화합물

HRID 2363164노트

반응식

HRID 2363164 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 67111294HCID 67111294, 화합물수율 77%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-ed58e750fd3d4bb286823af892ad1a67
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691855B2

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