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Dichloromethane → HCID 136117292, 화합물

HRID 78649
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HRID 78649 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.[C:34]([O-:37])(=O)[CH3:35].[K+].C(Cl)Cl.[NH2:42][C:43]1[C:44]([C:50]2[O:54][C:53]([C:55]3[CH:60]=CC(CC([O-])=O)=[CH:57][CH:56]=3)=[N:52][N:51]=2)=[N:45][C:46](Br)=[CH:47][N:48]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CN(C=O)C.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>[NH2:42][C:43]1[C:44]([C:50]2[O:54][C:53]([C:55]3[CH:60]=[CH:35][C:34]([OH:37])=[CH:57][CH:56]=3)=[N:52][N:51]=2)=[N:45][C:46]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:47][N:48]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 6

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 68494241HCID 68494241, 화합물HCID 86645024[4-[5-(3-Amino-6-bromo-pyrazin-2-yl)-1,3,4-oxadiazol-2-yl]phenyl]acetate

생성물 1

HCID 136117292
HCID 136117292, 화합물
수율 15.3%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

2-(4-bromophenyl)sulfonyl-N,N-dimethyl-ethanamine (181.8 mg, 0.6221 mmol) was dissolved in dioxane (2 mL) and bis(pinacolato)diboron (237.0 mg, 0.9332 mmol) and potassium acetate (183.1 mg, 1.866 mmol) were added. The reaction mixture was degassed and filled with nitrogen (5×) then Pd(dppf)Cl2.CH2Cl2 (50.80 mg, 0.06221 mmol) was added and the reaction heated to 90° C. for 2 hours. The reaction mixture was cooled to ambient temperature and diluted with DMF (2 mL). [4-[5-(3-amino-6-bromo-pyrazin-2-yl)-1,3,4-oxadiazol-2-yl]phenyl]acetate (234 mg, 0.6221 mmol), Na2CO3 (933.0 μL of 2 M aqueous solution, 1.866 mmol) and Pd(PPh3)2Cl2 (43.67 mg, 0.06221 mmol) were added and the reaction heated at 150° C. under microwave conditions for 30 minutes. The reaction mixture was partitioned between EtOAc (5 mL) and water (5 mL) and any precipitate removed by filtration. The layers were separated and the aqueous layer extracted with EtOAc (3×5 mL) and the combined organic extracts dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated form EtOAc/MeOH to give the title compound as a brown solid (44.3 mg, 15%); 1H NMR (400 MHz, DMSO) d 2.07 (s, 6H), 2.56 (t, 2H), 3.52 (t, 2H), 7.03 (d, 2H), 7.87 (br s, 2H), 8.02 (dd, 4H), 8.38 (d, 2H), 9.05 (s, 1H) and 10.44 (s, 1H) ppm; MS (ES+) 467.2

후처리

  1. customThe reaction mixture was degassed
  2. additionfilled with nitrogen (5×)
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. temperaturethe reaction heated at 150° C. under microwave conditions for 30 minutes
  5. customThe reaction mixture was partitioned between EtOAc (5 mL) and water (5 mL)
  6. customany precipitate removed by filtration
  7. customThe layers were separated
  8. extractionthe aqueous layer extracted with EtOAc (3×5 mL)
  9. dry with materialthe combined organic extracts dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was triturated form EtOAc/MeOH

출처 및 근거

ORD 기록
ord-6d66e792de94473abb6dc021155ba898
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841308B2

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