Methyl 3-bromothiophene-2-carboxylate → 3-(6-Phenylpyridazin-4-yl)thiophene-2-carboxylic Acid Methyl Ester

HRID 130338

반응식

HRID 130338 반응식
[C:1]1([C:7]2[N:8]=[N:9][CH:10]=[C:11]([Sn](CCCC)(CCCC)CCCC)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:27]1[CH:31]=[CH:30][S:29][C:28]=1[C:32]([O:34][CH3:35])=[O:33]>C1COCC1.C(Cl)Cl.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:35][O:34][C:32]([C:28]1[S:29][CH:30]=[CH:31][C:27]=1[C:11]1[CH:12]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[N:9][CH:10]=1)=[O:33]

참가 물질

7

반응물 2

HCID 2740074Methyl 3-bromothiophene-2-carboxylateHCID 11729979Pyridazine, 3-phenyl-5-(tributylstannyl)-

생성물 1

HCID 99717923-(6-Phenylpyridazin-4-yl)thiophene-2-carboxylic Acid Methyl Ester수율 12%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
150 °C

실험 절차

3-Phenyl-5-(tri-n-butylstannyl)pyridazine (50 mg, 0.11 mmol), methyl 3-bromothiophene-2-carboxylate (30 mg) and Pd(PPh3)4 (5 mg) in THF (2 ml) were combined and heated to 150° C. for 600 seconds in a Smith Synthesizer microwave reactor. The reaction was diluted with CH2Cl2 (6 ml) and H2O (2 ml) then poured into PTFE (5 μM) fritted syringe barrels. The organic phase was collected and concentrated to leave 85 mg of crude product. Part of the sample was purified by HPLC with mass triggered collection of fractions to give the title compound (3.9 mg). δH (400 MHz, d6 DMSO) 3.73 (3H, s), 7.52-7.62 (4H, m), 8.10 (1H, d, J 8.0), 8.22 (2H, dd, J 1.6 and 8.0), 8.35 (1H, d, J 4.0), 9.33 (1H, d, J 4.0); m/z (ES+) (MH+) 297.

후처리

  1. additionthen poured into PTFE (5 μM) fritted syringe barrels
  2. customThe organic phase was collected
  3. concentrationconcentrated
  4. customto leave 85 mg of crude product
  5. customPart of the sample was purified by HPLC with mass
  6. customcollection of fractions

출처 및 근거

ORD 기록
ord-a689d9e8eb8b4e87821e88b3fa1c8f20
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381725B2

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