Tetrahydrofuran → 3-Bromo-5-(1-ethenylcyclopropyl)pyridine

HRID 1521614Notes

Reaction equation

HRID 1521614 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH:11]=O)[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.O1CCC[CH2:14]1>>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2([CH:11]=[CH2:14])[CH2:10][CH2:9]2)[CH:3]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 891558951-(5-Bromopyridin-3-yl)cyclopropane-1-carbaldehyde

Product 1

HCID 891559033-Bromo-5-(1-ethenylcyclopropyl)pyridine

Procedure

To a solution of methyltriphenylphosphonium bromide-sodium amide complex (510 mg, 01.22 mmol) in tetrahydrofuran (2.0 mL) was added a solution of the title compound from Example 73 Step B (97 mg, 0.43 mmol) in tetrahydrofuran (1.0 mL) The reaction stirred at room temperature for 16 hours. It was then quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The organic extracts were combined, washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0-100% ethyl acetate in hexanes) provided the title compound: LCMS m/z 225.77 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 8.54 (s, 1H), 8.47 (s, 1H), 7.50 (s, 1H), 5.68 (dd, J=10.4, 17.1, 1 H), 4.98 (d, J=10.4, 1 H), 4.62 (d, J=17.1, 1 H), 1.12-1.05 (m, 4H).

Workup

  1. customIt was then quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography on silica gel (0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7c99dd656bf442f3a9073ab8908bb57e
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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