4-Vinylpyridine → HCID 54034311, compound

HRID 365856Notes

Reaction equation

HRID 365856 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:EtOAc 1:3 to afford the title compound (440 mg, 79% yield). MS (CI/NH3) m/z 382 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.49 (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, 0.5 H), 8.22-8.42 (m, 1.5 H), 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:EtOAc 1:3

Sources & evidence

ORD record
ord-77a8f99e9e7a41c09a8bb7a3d74b0850
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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