Triethylamine → 2-Bromo-5-fluoro-4-isopropenyl-pyridine

HRID 538339ノート

反応式

HRID 538339 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([C:8](O)([CH3:10])[CH3:9])[C:5]([F:12])=[CH:4][N:3]=1.CS(OS(C)(=O)=O)(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[CH2:9])[C:5]([F:12])=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 81560Methanesulfonic anhydride2 回HCID 866680482-Bromo-5-fluoro-alpha,alpha-dimethyl-4-pyridinemethanol

生成物 1

HCID 866680492-Bromo-5-fluoro-4-isopropenyl-pyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(2-bromo-5-fluoro-pyridin-4-yl)-propan-2-ol (24.7 g, 106 mmol) and methanesulfonic anhydride (55.1 g, 317 mmol) in DCM (250 ml) was added triethylamine (58.8 ml, 42.7 g, 422 mmol). The reaction mixture was stirred at rt for 20 h. Another 1 eq. (18 g) of methanesulfonic anhydride and 1.2 eq. (17 ml) of triethylamine were added and the reaction mixture was stirred an additional 20 h at rt. The reaction mixture was quenched with 1M aq. Na2CO3 sol. and diluted with DCM. The phases were separated and the aq. phase was reextracted twice with DCM. The combined org. phases were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography on silica gel (hexane:EtOAc 8:1) yielded the title compound as a clear colourless liquid. HPLC RtH4=1.12 min; ESIMS: 216, 218 [(M+H)+]; 1H NMR (400 MHz, CDCl3): δ 8.20 (d, 1H), 7.40 (d, 1H), 5.48-5.44 (m, 2H), 2.14 (s, 3H).

後処理

  1. stirringthe reaction mixture was stirred an additional 20 h at rt
  2. customThe reaction mixture was quenched with 1M aq. Na2CO3 sol.
  3. additiondiluted with DCM
  4. customThe phases were separated
  5. washphases were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-924c90ec02c149b59cd7f4af962048e4
出典データセット
uspto-grants-2014_10
特許番号
US08865712B2

反応ノート

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