Sodium hydride → HCID 86623997, 화합물

HRID 1426725노트

반응식

HRID 1426725 반응식
[H-].[Na+].[F:3][C:4]1[C:5]([CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:6][NH:7][C:8]=1[C:9]1[C:10]([F:15])=[N:11][CH:12]=[CH:13][CH:14]=1.C1OCCOCCOCCOCCOC1.[CH3:41][C:42]1[O:46][C:45]([C:47]2[CH:48]=[C:49]([S:53](Cl)(=[O:55])=[O:54])[CH:50]=[CH:51][CH:52]=2)=[N:44][N:43]=1>O1CCCC1.O>[F:3][C:4]1[C:5]([CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[CH:6][N:7]([S:53]([C:49]2[CH:50]=[CH:51][CH:52]=[C:47]([C:45]3[O:46][C:42]([CH3:41])=[N:43][N:44]=3)[CH:48]=2)(=[O:55])=[O:54])[C:8]=1[C:9]1[C:10]([F:15])=[N:11][CH:12]=[CH:13][CH:14]=1

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 27796963-(5-methyl-1,3,4-oxadiazol-2-yl)benzenesulfonyl ChlorideHCID 67176761tert-butyl {[4-fluoro-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate

생성물 1

HCID 86623997HCID 86623997, 화합물수율 52%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of sodium hydride (60% in oil, 18 mg) in tetrahydrofuran (0.5 mL) were added dropwise a solution of tert-butyl {[4-fluoro-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate (97 mg) in tetrahydrofuran (0.5 mL), 15-crown-5 (100 mg) and 3-(5-methyl-1,3,4-oxadiazol-2-yl)benzenesulfonyl chloride (85 mg) under ice-cooling and the mixture was stirred for 2 hr. The reaction mixture was diluted with water, and extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→1:1) to give the title compound as a pale-yellow oil (yield 85 mg, 52%).

후처리

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. extractionThe separated aqueous layer was extracted again with ethyl acetate
  4. washThe combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→1:1)

출처 및 근거

ORD 기록
ord-93a35494b9d34d3f892f1984a5efd206
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933105B2

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