Phenyl Isothiocyanate → 3-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridine-1-carbothioic acid phenylamide

HRID 1820885

反応式

HRID 1820885 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].[N:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[C:23]=[S:24]>CN(C)C=O>[C:25]1([NH:22][C:23]([N:13]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:19]3[C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:12]2)=[S:24])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

5

反応物 3

HCID 7673Phenyl IsothiocyanateHCID 24758Sodium hydrideHCID 116732853-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 578917683-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridine-1-carbothioic acid phenylamide収率 49%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-(3,4-Dimethoxy-phenyl)-1H-pyrrolo-[2,3-b]pyridine 1 (50 mg, 0.20 mmol) was dissolved in N,N-dimethylformamide (4 mL). Sodium hydride (10 mg, 0.24 mmol, 60% dispersion in mineral oil) was added. The reaction mixture was stirred for 15 minutes at room temperature. 1-Isothiocyanatobenzene (35 μL, 0.29 mmol) was added and the reaction mixture was stirred for 40 minutes at room temperature. The product was concentrated and the residue was partitioned between brine and ethyl acetate. The organic portion was dried over anhydrous sodium sulfate, filtered, and concentrated to provide a solid. The solid was washed with a minimum of methanol and dried in vacuo to provide 41, (38 mg, 49%). MS(ESI) [M+H+]+=390.2.

後処理

  1. stirringthe reaction mixture was stirred for 40 minutes at room temperature
  2. concentrationThe product was concentrated
  3. customthe residue was partitioned between brine and ethyl acetate
  4. dry with materialThe organic portion was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide a solid
  8. washThe solid was washed with a minimum of methanol
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-3efaeec05f0a4d48a7a64444d7895e97
出典データセット
uspto-grants-2009_10
特許番号
US07605168B2

関連ノート

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