Methanol → (5-Bromo-6-(2,4-difluorophenoxy)pyridin-3-yl)methanol

HRID 930934노트

반응식

HRID 930934 반응식
[Br:1][C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].CO>O1CCCC1>[Br:1][C:2]1[CH:10]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19]

참가 물질

4

반응물 2

HCID 887MethanolHCID 867210745-Bromo-6-(2,4-difluorophenoxy)nicotinic acid

생성물 1

HCID 86721075(5-Bromo-6-(2,4-difluorophenoxy)pyridin-3-yl)methanol수율 76.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

The product from Example 311a (1.0 g, 3.03 mmol) and borane tetrahydrofuran complex (6.06 mL, 6.06 mmol) were combined in tetrahydrofuran (15.15 mL) and heated at 50° C. for 2 hours, cooled, treated with 10 mL of methanol, heated at 50° C. for 1 hour, cooled and concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (Na2SO4), filtered, and concentrated. Purification by chromatography (silica gel, 0-50% ethyl acetate in heptanes) afforded the title compound (0.73 g, 76%).

후처리

  1. temperaturecooled
  2. temperatureheated at 50° C. for 1 hour
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe residue was partitioned between ethyl acetate and water
  6. washThe organic layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by chromatography (silica gel, 0-50% ethyl acetate in heptanes)

출처 및 근거

ORD 기록
ord-e9d620f55da54434a8eef52e24f05f50
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296741B2

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