4-Vinylpyridine → HCID 54034311, compound

HRID 1780359Notes

Reaction equation

HRID 1780359 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:5]=[N:6][CH:7]=1.[CH:22]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)=[CH2:23].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C>[N:27]1[CH:28]=[CH:29][C:24]([CH:22]=[CH:23][C:2]2[CH:3]=[C:4]([O:8][CH2:9][C@H:10]3[CH2:14][CH2:13][CH2:12][N:11]3[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:5]=[N:6][CH:7]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 75024-VinylpyridineHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 154802363-bromo-5-[[1-(tert-butoxycarbonyl)-2(R)-pyrrolidinyl]methoxy]pyridine

Product 1

HCID 54034311HCID 54034311, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromo-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)pyridine (440 mg, 1.25 mmol), 4-vinylpyridine (0.267 mL), Pd(OAc)4 (30 mg), tris(o-tolyl)phosphine (160 mg), and triethylamine (3.5 mL) in acetonitrile (4 mL) was heated at reflux for 16 hours. The solution was then concentrated, and the residue was washed with water and aqueous NaHCO3 solution. The organic layer was dried and concentrated. The residue was chromatographed on a silica gel column, eluting with hexane:ethyl acetate 1:3 to afford the title compound (440 mg, 79% yield). MS (DCI/NH3) m/z 382 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 1.49 (s, 3H), 1.85-2.12 (m, 4H), 3/26-3.55 (m, 2H), 3.86-4.08 (m, 1H), 4.08-4.34 (m, 1H), 7.20-7.30 (m, 2H), 7.36-7.42 (m, 2H), 7.71 (br s, 0.5H), 8.22-8.42 (m, 1.5H), 8.58-8.69 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. concentrationThe solution was then concentrated
  4. washthe residue was washed with water and aqueous NaHCO3 solution
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a silica gel column
  8. washeluting with hexane:ethyl acetate 1:3

Sources & evidence

ORD record
ord-047174515faf45ec8ba5027d896bba34
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

Loading…