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Dichloromethane → HCID 136117292、化合物

HRID 78649
ノート
印刷プレビュー

反応式

HRID 78649 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 6

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

生成物 1

HCID 136117292
HCID 136117292、化合物
収率 15.3%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-6d66e792de94473abb6dc021155ba898
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08841308B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート