Sodium Hydroxide → 3-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-(methylsulfonyl)pyrazolo[5,1-b][1,3]thiazole

HRID 41268노트

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HRID 41268 반응식
Br[C:2]1[CH:22]=[C:5]2[S:6][CH:7]=[C:8]([C:9]3[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH2:17][O:18][CH3:19])=[CH:11][C:10]=3[O:20][CH3:21])[N:4]2[N:3]=1.[CH3:23][S:24]([O-:26])=[O:25].[Na+].N1CCC[C@H]1C(O)=O.[OH-].[Na+]>[Cu](I)I.O.CS(C)=O>[CH3:21][O:20][C:10]1[CH:11]=[C:12]([CH2:17][O:18][CH3:19])[CH:13]=[C:14]([O:15][CH3:16])[C:9]=1[C:8]1[N:4]2[N:3]=[C:2]([S:24]([CH3:23])(=[O:26])=[O:25])[CH:22]=[C:5]2[S:6][CH:7]=1

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 2733271Sodium methanesulfinateHCID 582234186-Bromo-3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[5,1-b][1,3]thiazole

생성물 1

HCID 582234563-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-(methylsulfonyl)pyrazolo[5,1-b][1,3]thiazole수율 89.7%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
140 °C

실험 절차

To a dimethyl sulfoxide (28.0 mL) solution of 6-bromo-3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[5,1-b][1,3]thiazole (1.12 g, 2.92 mmol) were added sodium methanesulphinate (2.38 g, 23.3 mmol), L-proline (268 mg, 2.33 mmol), sodium hydroxide (184 mg, 4.61 mmol), and copper iodide (444 mg, 2.33 mmol) and the mixture was heated at 140° C. for three hours by using Biotage Initiator™ Microwave Synthesizer. After the reaction was completed, water was added, the reaction mixture was extracted with ethyl acetate, the organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. To the residue, ethyl acetate was added, and the obtained solid was subjected to suction filtration and dried to obtain the title compound (1.00 g, 2.62 mmol).

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionTo the residue, ethyl acetate was added
  5. filtrationthe obtained solid was subjected to suction filtration
  6. customdried

출처 및 근거

ORD 기록
ord-b3466e03091f4f59a6c842bb8b7abe9c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530504B2

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