Potassium Carbonate → Methyl 5-(benzyloxy)-2-(4-fluorophenyl)furo[2,3-c]pyridine-3-carboxylate

HRID 219381

반응식

HRID 219381 반응식
[C:1]([O-])(=O)C.[Na+].[C:6]([O-:9])([O-])=[O:7].[K+].[K+].[CH2:12]([O:19][C:20]1[N:25]=[CH:24][C:23]([OH:26])=[C:22]([C:27]#[C:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO.O.O.[Cu](Cl)Cl.[Pd](Cl)Cl>[CH2:12]([O:19][C:20]1[CH:21]=[C:22]2[C:27]([C:6]([O:9][CH3:1])=[O:7])=[C:28]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[O:26][C:23]2=[CH:24][N:25]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 517045Sodium AcetateHCID 672172956-(Benzyloxy)-4-((4-fluorophenyl)ethynyl)pyridin-3-ol

생성물 1

HCID 67217578Methyl 5-(benzyloxy)-2-(4-fluorophenyl)furo[2,3-c]pyridine-3-carboxylate수율 100%

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 61482Cupric chloride dihydrate촉매HCID 887Methanol용매

실험 절차

Sodium acetate (1.14 g, 13.9 mmol), K2CO3 (1.92 g, 13.9 mmol), copper (II) chloride dihydrate (3.56 g, 20.9 mmol), palladium (II) chloride (0.205 g, 1.15 mmol) was added to a stirring solution of 6-(benzyloxy)-4-((4-fluorophenyl)ethynyl)pyridin-3-ol (2.22 g, 6.95 mmol) in MeOH (150 mL) at room temperature in a Parr Bomb. The vessel was charged with 300 PSI of CO (g) and allowed to stir at room temperature overnight. The mixture was concentrated then diluted with EtOAc and washed with H2O, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to give the expected product methyl 5-(benzyloxy)-2-(4-fluorophenyl)furo[2,3-c]pyridine-3-carboxylate (2.62 g, 6.95 mmol, 100% yield) by LCMS. LC-MS retention time: 2.66 min; m/z (MH+): 378. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters SunFire 5u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% acetonitrile/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% acetonitrile/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode.

후처리

  1. additionThe vessel was charged with 300 PSI of CO (g)
  2. concentrationThe mixture was concentrated
  3. additionthen diluted with EtOAc
  4. washwashed with H2O
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-60dcdc3ccd354703baa02462f8d478dc
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198449B2

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