Triethylamine → HCID 22872639、化合物

HRID 2305134ノート

反応式

HRID 2305134 の反応式
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:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(N(CC)CC)C>C(Cl)Cl.[Cu]I>[C:23]([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])#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 123701-OctyneHCID 22872666HCID 22872666、化合物

生成物 1

HCID 22872639HCID 22872639、化合物収率 72.3%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 5-bromo-6-chloro-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)pyridine from Example 69a (425 mg, 1.1 mmol), 1-octyne (0.2 mL, 1.4 mmol), Pd(PPh)3Cl2 (20 mg), CuI (catalytic amount) and triethylamine (0.5 mL) in CH2Cl2 (8 mL) was heated at reflux for 16 hours. Heating was continued until no starting material remained. The solvent was removed, and the residue was washed with 10% NaOH then extracted with CH2Cl2. The organic extract was dried over MgSO4 and concentrated. The residue was chromatographed on a silica gel column, eluting with hexane:Et2O 100:6-100:15 to afford to give the title compound (335 mg, 72% yield). MS (CI/NH3) m/z 421 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 0.90 (m, 3H), 1.32 (m, 4H), 1.48 (s, 9H), 1.49 (m, 2H), 1.62 (m, 2H), 1.88 (m, 2H), 2.00 (m, 2H), 2.48 (m, 2H), 3.34 (m, 2H), 3.90 (m, 1H), 4.12 (m, 2H), 7.30 (br s, 1H), 7.98 (m, 1H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. temperatureHeating
  4. customThe solvent was removed
  5. washthe residue was washed with 10% NaOH
  6. extractionthen extracted with CH2Cl2
  7. extractionThe organic extract
  8. dry with materialwas dried over MgSO4
  9. concentrationconcentrated
  10. customThe residue was chromatographed on a silica gel column
  11. washeluting with hexane:Et2O 100:6-100:15
  12. customto afford

出典と根拠

ORDレコード
ord-c044bb1ffcad40da83e73af65c47f497
出典データセット
uspto-grants-2002_08
特許番号
US06437138B1

反応ノート

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