Potassium Carbonate → 4-(5-Chloro-2-hydroxyphenyl)pyridine-2-carbaldehyde

HRID 46395

반응식

HRID 46395 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6](B(O)O)[CH:7]=1.Br[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([CH:19]=[O:20])[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C(OCC)(=O)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH:19]=[O:20])[CH:14]=2)[CH:7]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 147614724-Bromopyridine-2-carbaldehydeHCID 23005362(5-Chloro-2-hydroxyphenyl)boronic Acid (contains varying amounts of Anhydride)

생성물 1

HCID 1360636234-(5-Chloro-2-hydroxyphenyl)pyridine-2-carbaldehyde수율 22.1%

시약·촉매·용매 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

(5-Chloro-2-hydroxyphenyl) boronic acid (1.58 g, 0.00914 mol) was combined with 4-bromopyridine-2-carbaldehyde (1.70 g, 0.0091 mol), bis(triphenylphosphine)palladium (II) chloride (0.321 g, 0.00046 mol) and potassium carbonate (3.16 g, 0.0228 mol) in a 5 mL microwave vial. 1,4-dioxane (3 mL) and water (0.2 mL) were added and heated to 100° C. for 50 minutes in the microwave. The reaction was diluted with ethyl acetate (30 mL) and water (20 mL), filtered, the organic phase was separated then dried over anhydrous sodium sulphate, concentrated in vacuo and purified by flash column chromatography, ISCO™ (80 g column, eluting with 100% heptane to 50% v/v ethyl acetate in heptane) to give the title compound as a beige solid (0.47 g).

후처리

  1. filtrationfiltered
  2. customthe organic phase was separated
  3. dry with materialthen dried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo
  5. custompurified by flash column chromatography, ISCO™ (80 g column
  6. washeluting with 100% heptane to 50% v/v ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-63765137801a43b0b79bba7986e4c2d9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541588B2

연결된 노트

불러오는 중…