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

HRID 1526610ノート

反応式

HRID 1526610 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-85f7ac6c2f7f4f9bb4092c505142fffc
出典データセット
uspto-grants-2015_07
特許番号
US09085576B2

反応ノート

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