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

HRID 130338

反応式

HRID 130338 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.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]

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a689d9e8eb8b4e87821e88b3fa1c8f20
出典データセット
uspto-grants-2008_06
特許番号
US07381725B2

関連ノート

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