4-Bromopyridinium chloride → Pyridazine, 3-phenyl-5-(4-pyridinyl)-

HRID 130337

반응식

HRID 130337 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.Cl.Br[C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1>C1COCC1.C(Cl)Cl.[NH4+].[Cl-].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>[C:1]1([C:7]2[N:8]=[N:9][CH:10]=[C:11]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

7

반응물 2

HCID 881004-Bromopyridinium chlorideHCID 11729979Pyridazine, 3-phenyl-5-(tributylstannyl)-

생성물 1

HCID 10198553Pyridazine, 3-phenyl-5-(4-pyridinyl)-수율 69.4%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매

반응 조건

온도
150 °C

실험 절차

3-Phenyl-5-(tri-n-butylstannyl)pyridazine (110 mg, 0.247 mmol), 4-bromopyridine hydrochloride (72 mg, 0.370 mmol) and Pd(PPh3)4 (10 mg) in THF (2 ml) were combined and heated to 150° C. for 60 min in a Smith Synthesiser microwave reactor (Personal Chemistry, Uppsala, Sweden). The reaction was diluted with CH2Cl2 (6 ml) and NH4Cl (2 ml) then poured into PTFE (5 μM) fritted syringe barrels. The organic phase was collected and concentrated while loading onto silica. The compound was purified by dry flash column chromatography to give the title compound as a white solid (40 mg). δH (400 MHz, d6 DMSO) 7.36-7.63 (3H, m), 8.10 (2H, dd, J 1.8 and 4.5), 8.32 (2H, m), 8.62 (1H, d, J 2.0), 8.80-8.82 (2H, dd, J 1.8 and 4.5), 9.71 (2H, d, J 2.0); m/z (ES+) 234 (MH+).

후처리

  1. additionthen poured into PTFE (5 μM) fritted syringe barrels
  2. customThe organic phase was collected
  3. concentrationconcentrated
  4. customThe compound was purified
  5. customby dry flash column chromatography

출처 및 근거

ORD 기록
ord-6ab7387de01244b79f01f726fa6820c7
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381725B2

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