Pyridazine → (R)-3-(4-Bromophenyl)-1-(pyridazin-4-yl)-3-o-tolylpropan-1-one

HRID 1527964ノート

反応式

HRID 1527964 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][N:2]=1.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH2:15][C:16](N(OC)C)=[O:17])=[CH:10][CH:9]=1.CC(N=P(N=P(N(C)C)(N(C)C)N(C)C)(N=P(N(C)C)(N(C)C)N(C)C)N=P(N(C)C)(N(C)C)N(C)C)(C)C>C1COCC1.[I-].[Zn+2].[I-]>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C@H:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH2:15][C:16]([C:5]2[CH:4]=[CH:3][N:2]=[N:1][CH:6]=2)=[O:17])=[CH:12][CH:13]=1

参加物

6

反応物 3

HCID 9259PyridazineHCID 4339838N'''-(1,1-Dimethylethyl)-N,N',N''-tris(tris(dimethylamino)phosphoranylidene)phosphorimidic triamideHCID 71813344(R)-3-(4-Bromophenyl)-N-methoxy-N-methyl-3-o-tolylpropanamide

生成物 1

HCID 86684791(R)-3-(4-Bromophenyl)-1-(pyridazin-4-yl)-3-o-tolylpropan-1-one収率 3%

試薬・触媒・溶媒 2

HCID 9883512zinc(II)iodide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of pyridazine (250 mg, 3.12 mmol) and (R)-3-(4-bromophenyl)-N-methoxy-N-methyl-3-o-tolylpropanamide (1.81 g, 4.99 mmol) in THF (10 mL) was added zinc iodide (996 mg, 3.12 mmol). The suspension was stirred for 10 min. at ambient temperature. The reaction mixture was cooled to −78° C., then N′″-(1,1-dimethylethyl)-N,N′,N″-tris[tris(dimethyl-amino)phosphoranylidene]-phosphorimidic triamide solution (“Schwesinger P4 base”; 1 M in hexane 4.68 mL, 4.68 mmol) was added. The reaction mixture was allowed to reach room temperature over 16 h, then partitioned between sat, aq. ammonium chloride solution and dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced the title compound 30 mg, 3%), while the most of the starting material was recovered (1.51 g, 83%). Light yellow gum, MS: 381.1 [M+H]+.

後処理

  1. temperatureThe reaction mixture was cooled to −78° C.
  2. waitto reach room temperature over 16 h
  3. custompartitioned
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-70e44b26244040a998e197a5250a6a87
出典データセット
uspto-grants-2015_07
特許番号
US09090565B2

反応ノート

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