4-Vinylpyridine → HCID 54192485, 화합물

HRID 365853노트

반응식

HRID 365853 반응식
Br[C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:5]=[N:6][C:7]=1[Cl:8].[CH:23]([C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)=[CH2:24].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C>[N:28]1[CH:29]=[CH:30][C:25]([CH:23]=[CH:24][C:2]2[CH:3]=[C:4]([O:9][CH2:10][C@H:11]3[CH2:15][CH2:14][CH2:13][N:12]3[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:5]=[N:6][C:7]=2[Cl:8])=[CH:26][CH:27]=1

참가 물질

6

반응물 4

HCID 75024-VinylpyridineHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 22872666HCID 22872666, 화합물

생성물 1

HCID 54192485HCID 54192485, 화합물수율 69%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 5-bromo-6-chloro-3-(1-BOC-2-(R)-pyrrolidinyimethoxy)pyridine from Example 69a (1.18 g, 3 mmol), 4-ethenylpyridine (0.39 mL, 3.6 mmol), Pd(OAc)4 (62.5 mg), tris(o-tolyl)phosphine (312.5 mg), and triethylamine (6.25 mL) in acetonitrile (15 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:Et2O 100:5-100:15 to afford the title compound (852 mg, 69% yield). MS (CI/NH3) m/z 416 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.48 (s, 9H), 1.92 (m, 2H), 2.02 (m, 2H), 3.42 (m, 2H), 3.97 (m, 1H), 4.13 (m, 2H), 7.43 (m, 2H), 7.56 (m, 1H), 8.05 (m, 1H), 8.62 (m, 2H).

후처리

  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:Et2O 100:5-100:15

출처 및 근거

ORD 기록
ord-6688ede8bee34979a187c2b687100952
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06127386

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