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

HRID 130337

反応式

HRID 130337 の反応式
[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

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
150 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-6ab7387de01244b79f01f726fa6820c7
出典データセット
uspto-grants-2008_06
特許番号
US07381725B2

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