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Triethylamine → 5-Bromo-2-(3-fluorooxetan-3-yl)pyridine

HRID 1500295
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HRID 1500295 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2(O)[CH2:11][O:10][CH2:9]2)=[N:6][CH:7]=1.F.F.F.C(N(CC)CC)C.C(N(CC)CC)C.[F:30][B-](F)(F)F.C(N([S+](F)F)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([F:30])[CH2:11][O:10][CH2:9]2)=[N:6][CH:7]=1
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 44517918(Diethylamino)difluorosulfonium tetrafluoroborate2회HCID 867131693-(5-Bromopyridin-2-yl)oxetan-3-ol

생성물 1

HCID 867131825-Bromo-2-(3-fluorooxetan-3-yl)pyridine수율 66.3%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
3회

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온도
0 °C

실험 절차

A solution of the product of Step 1, Example 8 (300.0 mg, 1.30 mmol) in methylene chloride (3.00 mL) is added to a mixture of triethylamine trishydrofluoride (0.531 mL, 3.26 mmol), triethylamine (0.273 mL, 1.96 mmol), and (Diethylamino)difluorosulfonium tetrafluoroborate (597 mg, 2.61 mmol) in methylene chloride (20.0 mL) at −78° C. The reaction mixture is slowly allowed to warm to 0° C. More (Diethylamino)difluorosulfonium tetrafluoroborate (100.0 mg, 0.437 mmol) is added and stirring continued at this temperature for 1 hour. The mixture is diluted with methylene chloride, washed with saturated sodium hydrogen carbonate solution, brine, dried over magnesium sulfate, and then concentrated. The residue is purified by chromatography on silica gel eluting with a gradient of 0-30% ethyl acetate to afford the title compound (200 mg): MS (ESI+) m/z 232.1/234.1 [M+H].

후처리

  1. washwashed with saturated sodium hydrogen carbonate solution, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue is purified by chromatography on silica gel eluting with a gradient of 0-30% ethyl acetate

출처 및 근거

ORD 기록
ord-fe59a1bfb01a42ce923f0bf4800081e5
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09206126B2

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