Triethylamine → HCID 22872639, 화합물

HRID 2305147노트

반응식

HRID 2305147 반응식
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[C:16](Cl)=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:23]#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].CCN(CC)CC>C(Cl)Cl.[Cu]I>[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][C:18]([Cl:21])=[C:19]([C:23]#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 123701-OctyneHCID 22961842HCID 22961842, 화합물

생성물 1

HCID 22872639HCID 22872639, 화합물수율 78%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-chloro-6-chloropyridine from Example 69a (400 mg, 1.02 mmol), 1-octyne (0.23 mL, 1.54 mmol), Pd(PPh)3Cl2 (36 mg), CuI (catalytic amount) and NEt3 (2.5 mL) in CH2Cl2 (8 mL) was heated at reflux for 16 h. 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 (MgSO4) and concentrated. The residue was chromatographed (silica gel; hexane:EtOAc, 3:1) to afford the title compound (335 mg, 72% yield): 1H NMR (CDCl3, 300 MHz) δ 0.91 (t, J=7.5 Hz, 3H), 1.23-1.40 (m, 4H), 1.48 (s, 9H), 1.56-1.69 (m, 2H), 1.81-2.06 (m, 5H), 2.46 (t, J=7.5 Hz, 2H), 3.27-3.47 (m, 2H), 3.98-4.21 (m, 4H), 7.29 (br, s, 1H), 7.98 (d, J=3.0 Hz, 1H); MS (CI/NH3) m/z 421 (M+H)+.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  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 (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was chromatographed (silica gel; hexane:EtOAc, 3:1)

출처 및 근거

ORD 기록
ord-11df248c6c9e4ba68979b68b2b0e59b8
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06437138B1

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