Water → 2-[4-[4-(2-Methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-butyl]-7-azaindole

HRID 53222

반응식

HRID 53222 반응식
C([SiH](CC)CC)C.[CH3:8][N:9]1[N:13]=[N:12][C:11]([C:14]2[CH:34]=[C:33]([CH3:35])[C:17]([O:18][CH2:19][CH2:20][CH2:21][CH:22]([C:24]3[NH:25][C:26]4[C:31]([CH:32]=3)=[CH:30][CH:29]=[CH:28][N:27]=4)O)=[C:16]([CH3:36])[CH:15]=2)=[N:10]1.O.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[CH3:8][N:9]1[N:13]=[N:12][C:11]([C:14]2[CH:34]=[C:33]([CH3:35])[C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:24]3[NH:25][C:26]4[C:31]([CH:32]=3)=[CH:30][CH:29]=[CH:28][N:27]=4)=[C:16]([CH3:36])[CH:15]=2)=[N:10]1

참가 물질

6

반응물 4

HCID 962WaterHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 190820142-[4-[4-(2-Methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-1-hydroxy-butyl]-7-azaindole

생성물 1

HCID 190820192-[4-[4-(2-Methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-butyl]-7-azaindole수율 74%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

반응 조건

온도
20 °C

실험 절차

Triethylsilane (5 ml) was added to a stirred solution of 2-[4-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-1-hydroxy-butyl]-7-azaindole (520 mg, 1.33 mmol) in 20 ml of trifluoroacetic acid at 20° C. under nitrogen. The mixture was stirred at 20° C. for 10 min and then stirred at 70°-75° C. for 16 h. To the mixture was added water, and basified with an aqueous sodium bicarbonate solution (to pH=8) followed by extraction with methylene chloride (3x). The combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (7.5 cm column, ethyl acetate/hexane, 1/5-8/1) . The mixture was recrystallized to afford 349 mg (74%) of 2-[4-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-butyl]-7-azaindole, as a white solid, m.p. 147°-150° C.

후처리

  1. stirringstirred at 70°-75° C. for 16 h
  2. extractionfollowed by extraction with methylene chloride (3x)
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica column chromatography (7.5 cm column, ethyl acetate/hexane, 1/5-8/1)
  6. customThe mixture was recrystallized

출처 및 근거

ORD 기록
ord-bfb4f366bccc4afb8e8ffb785b490cc5
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618821

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