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

HRID 1846233ノート

反応式

HRID 1846233 の反応式
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

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 167845palladium(II) acetate触媒HCID 16211205Tetraethylammonium chloride monohydrate触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-034d2291cbe0402eb05be66bb82eb74d
出典データセット
uspto-grants-2015_02
特許番号
US08952009B2

反応ノート

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