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

HRID 633555노트

반응식

HRID 633555 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 60A (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 (anhydrous 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 (anhydrous Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by chromatography (silica gel, 0-50% ethyl acetate in heptanes)

출처 및 근거

ORD 기록
ord-fde6517d98a84c2b88043aa5f380f0a8
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321764B2

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