Methanol → 3-bromo-5H,6H,7H-cyclopenta[b]pyridin-7-one

HRID 1526610노트

반응식

HRID 1526610 반응식
C(=[C:8]1/[CH2:9][CH2:10][C:11]2[C:12]/1=[N:13][CH:14]=[C:15]([Br:17])[CH:16]=2)/C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[OH:38]>C(Cl)Cl>[Br:17][C:15]1[CH:16]=[C:11]2[CH2:10][CH2:9][C:8](=[O:38])[C:12]2=[N:13][CH:14]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 11776TriphenylphosphineHCID 90415449(E)-7-benzylidene-3-bromo-6,7-dihydro-5H-cyclopenta[b]pyridine

생성물 1

HCID 468641583-bromo-5H,6H,7H-cyclopenta[b]pyridin-7-one수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of (E)-7-benzylidene-3-bromo-6,7-dihydro-5H-cyclopenta[b]pyridine (1.61 g, 5.63 mmol) in MeOH (75 mL) and DCM (75 mL) was cooled to −78° C. and a stream of ozone in oxygen was bubbled through the solution for 10 min until the solution turned light blue. Oxygen was pass through the solution for 10 min until the solution turned colorless. Triphenylphosphine (3.63 g, 13.8 mmol) was added and the reaction mixture was allowed to warm to room temperature. The reaction mixture was stirred at room temperature for 1.5 h and then concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (80 g, 30% to 70% EtOAc in heptane) to give 3-bromo-5H-cyclopenta[b]pyridin-7(6H)-one (1.14 g, 5.38 mmol, 96% yield) as a yellow solid. MS m/z=211.9 [M+H]+. Calculated for C8H6BrNO 211.0.

후처리

  1. customa stream of ozone in oxygen was bubbled through the solution for 10 min until the solution
  2. customfor 10 min
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel (80 g, 30% to 70% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-85f7ac6c2f7f4f9bb4092c505142fffc
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085576B2

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