Furan → HCID 15480239, 화합물

HRID 1780299노트

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HRID 1780299 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])(CC)C.B(OC)(OC)OC.C(=O)([O-])[O-].[Na+].[Na+].Br[C:25]1[CH:26]=[C:27]([O:31][CH2:32][C@@H:33]2[CH2:37][CH2:36][CH2:35][N:34]2[CH3:38])[CH:28]=[N:29][CH:30]=1.C(=O)(O)[O-].[Na+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1C=CC=CC=1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:25]1[CH:26]=[C:27]([O:31][CH2:32][C@@H:33]2[CH2:37][CH2:36][CH2:35][N:34]2[CH3:38])[CH:28]=[N:29][CH:30]=1

참가 물질

11

반응물 6

HCID 8029FuranHCID 8470Trimethyl borateHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 112887213-Bromo-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridineHCID 178418400CID 53628100

생성물 1

HCID 15480239HCID 15480239, 화합물수율 99%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 241Benzene용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of furan (1.45 mL, 20.0 mmol) in THF (30.0 mL) was added sec-butyllithium (1.3M, 7.69 mL, 10.0 mmol) at -78° C. After half an hour at this temperature, trimethyl borate (2.27 mL, 20.0 mmol) was added. The reaction mixture was stirred at -78° C. for one hour and slowly warmed up to room temperature. Solvent was removed, and benzene (10.0 mL), sodium carbonate (2.0M, 5.0 mL), tetrakis(triphenylphosphine)palladium(0) (175 mg) and 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine (1.36 g, 5.0 mmol) were added. The reaction mixture was refluxed overnight, then cooled to room temperature. Water (2 mL) was added, and solid sodium bicarbonate was added until the aqueous layer was saturated. The mixture was extracted with EtOAc, which was dried over MgSO4, filtered and concentrated. The residue was chromatographed on a silica gel column, eluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90 to afford an oil (1.27 g, 99%). MS (CI/NH3) m/z 259 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.70-2.22 (m, 4H), 2.28-2.40 (m, 1H), 2.51 (s, 3H), 2.66-2.75 (m, 1H), 3.10-3.18 (m, 1H), 3.97-4.11 (m, 2H), 6.51 (dd, J=4.8 Hz, J=3.6 Hz, 1H), 6.74 (d, J=4.9 Hz, 1H), 7.47 (dd, J=3.0 Hz, J=2.1 Hz, 1H), 7.53 (d, J=3.6 Hz, 1H), 8.22 (d, J=3.0 Hz, 1H), 8.54 (d, J=2.1 Hz, 1H).

후처리

  1. temperatureslowly warmed up to room temperature
  2. customSolvent was removed
  3. temperatureThe reaction mixture was refluxed overnight
  4. temperaturecooled to room temperature
  5. extractionThe mixture was extracted with EtOAc, which
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was chromatographed on a silica gel column
  10. washeluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90

출처 및 근거

ORD 기록
ord-c1ea9d07f34d4617901ea43ab1609779
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05629325

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