Sodium hydride → HCID 66747768, 화합물

HRID 2036000

반응식

HRID 2036000 반응식
[H-].[Na+].[NH2:3][C:4]1[C:9]([O:10][C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([OH:21])=[CH:18]3)=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][N:5]=1.CC1C=CC(S(O[CH2:33][C:34]([F:37])([F:36])[F:35])(=O)=O)=CC=1.[Cl-].[NH4+]>CS(C)=O.C1COCC1>[F:35][C:34]([F:37])([F:36])[CH2:33][O:21][C:17]1[CH:18]=[C:19]2[C:14]([CH:13]=[CH:12][C:11]([O:10][C:9]3[C:4]([NH2:3])=[N:5][CH:6]=[CH:7][CH:8]=3)=[CH:20]2)=[CH:15][CH:16]=1

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 667477657-[(2-Aminopyridin-3-yl)oxy]naphthalen-2-ol

생성물 1

HCID 66747768HCID 66747768, 화합물수율 16.9%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
120 °C

실험 절차

To a mixture of sodium hydride (60%, 116 mg), 7-[(2-aminopyridin-3-yl)oxy]naphthalen-2-ol (477 mg) and dehydrated THF (10 mL) was added a mixture of 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (370 mg) and dehydrated THF (5 mL) at room temperature. The reaction mixture was stirred at 70° C. over the weekend, DMSO (10.00 ml) was added and the mixture was stirred at 120° C. for 1 hr. The reaction mixture was added to a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (82 mg) as a pale-yellow viscous product.

후처리

  1. additionwas added
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-ee74351f9bb44fefb622a7655958eca8
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575154B2

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