Toluene → HCID 18396232、化合物

HRID 611591ノート

反応式

HRID 611591 の反応式
[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]

参加物

5

反応物 3

HCID 1140Toluene2 回HCID 10340Sodium CarbonateHCID 18396230HCID 18396230、化合物

生成物 1

HCID 18396232HCID 18396232、化合物収率 100%

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f62f9686c86645b2ae60ad13a0b7171b
出典データセット
uspto-grants-1999_12
特許番号
US06001849

反応ノート

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