2-Fluoropyridine → HCID 59255525, 화합물

HRID 78230

반응식

HRID 78230 반응식
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][C:7]=1[F:14].[H-].[Na+].F[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>CN(C)C=O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][O:13][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:8][C:7]=1[F:14]

참가 물질

5

반응물 3

HCID 97462-FluoropyridineHCID 24758Sodium hydrideHCID 59255152(4-[1,3]Dioxolan-2-yl-3-fluoro-phenyl)-methanol

생성물 1

HCID 59255525HCID 59255525, 화합물수율 64.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To an N,N-dimethylformamide solution (20 mL) of (4-[1,3]dioxolan-2-yl-3-fluoro-phenyl)-methanol (2.44 g, 12.3 mmol) described in Manufacturing Example 204-1-3 was added sodium hydride (537 mg, 14.8 mmol, 60% in oil), which was cooled to 0° C., after which 2-fluoropyridine (1.27 mL, 14.8 mmol) was added to this suspension, which was stirred for 2 hours at 60° C. The mixture was cooled to room temperature and partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:4) to obtain the title compound (2.17 g, 64%).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned into ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:4)

출처 및 근거

ORD 기록
ord-a790f8a1e8bd42aabfd8e774f9cef5b0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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