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

HRID 1527964노트

반응식

HRID 1527964 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 9883512zinc(II)iodide촉매HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-70e44b26244040a998e197a5250a6a87
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090565B2

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