Toluene → HCID 18396232, 화합물

HRID 611591노트

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HRID 611591 반응식
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[O:21][C:20]2[C:15](=[N:16][CH:17]=[C:18](Br)[CH:19]=2)[CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])([O-])=O.[Na+].[Na+].[C:29]1(C)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>[Pd]>[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[O:21][C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:19]=2)[CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

참가 물질

5

반응물 3

HCID 1140Toluene2회HCID 10340Sodium CarbonateHCID 18396230HCID 18396230, 화합물

생성물 1

HCID 18396232HCID 18396232, 화합물수율 100%

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

The 2-(1-BOC-2-(S)-pyrrolidinyl)-6-bromofuro[3,2-b]pyridine (0.2 g, 0.54 mmol) obtained from Example 46a above was dissolved in toluene (2 mL). Phenylbororic acid (0.19 g, 1.62 mmol), palladium (O) tetrakis(triphenyl phosphine) (40 mg) and 2 M Na2CO3 solution (1 mL) were then added to the toluene solution. The resultant mixture was heated under reflux for 16 h. The desired product was extracted with CH2Cl2, dried over MgSO4 and filtered. Solvent was then removed under reduced pressure and the residue was chromatographed (silica gel: Hexane/EtOAc, 5:1 to 2:1) to afford an oil (0.22 g, 100%). MS (CI/NH3) m/z: 365 (M+H)+; 1H NMR (CDCl3, 300 MHz) δ 1.32, 1.50 (2s, 9H), 1.90-2.22 (m, 3H), 2.30 (m, 1H), 3.42-3.73 (m, 2H), 4.97-5.20 (m, 1H), 6.92-7.02 (m, 1H), 7.33-7.66 (m, 5H), 7.93 (s, 1H), 8.90 (s, 1H).

후처리

  1. temperatureunder reflux for 16 h
  2. extractionThe desired product was extracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customSolvent was then removed under reduced pressure
  6. customthe residue was chromatographed (silica gel: Hexane/EtOAc, 5:1 to 2:1)

출처 및 근거

ORD 기록
ord-f62f9686c86645b2ae60ad13a0b7171b
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06001849

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