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

HRID 1500295
ノート
印刷プレビュー

反応式

HRID 1500295 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 44517918(Diethylamino)difluorosulfonium tetrafluoroborate2 回HCID 867131693-(5-Bromopyridin-2-yl)oxetan-3-ol

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
3 回

反応条件

温度
0 °C

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-fe59a1bfb01a42ce923f0bf4800081e5
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09206126B2

反応ノート

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