Triphenylphosphine → furo[3,2-b]pyridin-3(2H)-one

HRID 1846233노트

반응식

HRID 1846233 반응식
C=[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[O:4][CH2:3]1.C([O:14]C1C(Br)=NC=CC=1)C=C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])=O.[K+]>CN(C=O)C.O.[Cl-].C([N+](CC)(CC)CC)C.CCOC(C)=O.C([O-])(O)=O.[Na+].CC([O-])=O.CC([O-])=O.[Pd+2]>[O:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:2](=[O:14])[CH2:3]1

참가 물질

10

반응물 4

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 23028574Pyridine, 2-bromo-3-(2-propenyloxy)-HCID 89964775HCID 89964775, 화합물

생성물 1

HCID 14199079furo[3,2-b]pyridin-3(2H)-one

시약·촉매·용매 5

HCID 167845palladium(II) acetate촉매HCID 16211205Tetraethylammonium chloride monohydrate촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
110 °C

실험 절차

3-methylene-2,3-dihydrofuro[3,2-b]pyridine. To a solution of 3-(allyloxy)-2-bromopyridine (1 eq.) in DMF (0.2 M), PPh3 (0.25 eq.), Pd(OAc)2 (0.1 eq), and KOAc (5 eq.), is added, under an argon atmosphere, tetraethyl ammonium chloride hydrate (2 eq.). The flask is purged with argon for 15 min, and the resulting reaction mixture is stirred at 110° C. for 16 h. The reaction progress is monitored by TLC. The reaction mixture is diluted with EtOAc and saturated NaHCO3 solution. The organic layer is separated and dried over Na2SO4, and concentrated. The product that may be thus obtained is purified by column chromatography to afford the title compound.

후처리

  1. customThe flask is purged with argon for 15 min
  2. customthe resulting reaction mixture
  3. customThe organic layer is separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe product that may be thus obtained
  7. customis purified by column chromatography

출처 및 근거

ORD 기록
ord-034d2291cbe0402eb05be66bb82eb74d
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952009B2

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