Methanol → [5-(2,4-Dichloro-phenyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol

HRID 526685노트

반응식

HRID 526685 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[N:11][C:12]([CH3:18])=[C:13]([CH:17]=1)[C:14](O)=[O:15].B.CO>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:17]=[C:13]([CH2:14][OH:15])[C:12]([CH3:18])=[N:11][C:10]=1[C:19]1[CH:20]=[CH:21][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:23][CH:24]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 6331BoraneHCID 89907449HCID 89907449, 화합물

생성물 1

HCID 89907741[5-(2,4-Dichloro-phenyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 3 g of 5-(2,4-Dichloro-phenyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid in 60 ml of THF, were added dropwise 21 ml of a 1M solution of borane in THF at room temperature. Then the reaction mixture was heated to reflux for 10 h. The reaction mixture was cooled to room temperature and 20 ml of methanol were carefully added. The solvents were removed under reduced pressure and the residue was dissolved in ethyl acetate. The organic layer was washed with 1 M hydrochloric acid, saturated sodium chloride solution and saturated sodium hydrogen carbonate solution. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The product was obtained as a white solid and used without further purification. Yield: 2.2 g.

후처리

  1. temperatureThen the reaction mixture was heated
  2. temperatureto reflux for 10 h
  3. customThe solvents were removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe organic layer was washed with 1 M hydrochloric acid, saturated sodium chloride solution and saturated sodium hydrogen carbonate solution
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe product was obtained as a white solid
  10. customused without further purification

출처 및 근거

ORD 기록
ord-996fb495400a403ba67dcd0ecac29b02
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346757B2

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