Acetic Acid → 2,3-dihydro-1H-[2,3']bipyridinyl-4-one

HRID 1691833노트

반응식

HRID 1691833 반응식
C[Si](C)(C)CCS([N:8]1[CH:13]=[CH:12][C:11](=[O:14])[CH2:10][CH:9]1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)(=O)=O.[F-].[Cs+].C(O)(=O)C>CN(C=O)C.C(OCC)(=O)C>[NH:8]1[CH:13]=[CH:12][C:11](=[O:14])[CH2:10][CH:9]1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 25953Cesium fluorideHCID 593777611-(2-trimethylsilyl-ethanesulfonyl)-2,3-dihydro-1H-[2,3']bipyridinyl-4-one

생성물 1

HCID 593777842,3-dihydro-1H-[2,3']bipyridinyl-4-one수율 94.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

To a solution of 1-(2-trimethylsilyl-ethanesulfonyl)-2,3-dihydro-1H-[2,3′]bipyridinyl-4-one (106.1 mg, 0.31 mmol) in DMF (0.5 mL) was added cesium fluoride (153.5 mg, 1.0 mmol) under Ar atmosphere. The mixture was heated at 90° C. for 2 hours, then cooled to room temperature. Acetic acid (0.062 mL, 1.085 mmol) was added, and the mixture was diluted with ethyl acetate and filtered. The filtrate was taken to dryness under reduced pressure. Purification of the residue by flash chromatography (dichloromethane/methanol 95:5) gave 2,3-dihydro-1H-[2,3′]bipyridinyl-4-one (51 mg, 93.5%).

후처리

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customPurification of the residue by flash chromatography (dichloromethane/methanol 95:5)

출처 및 근거

ORD 기록
ord-3ddaee935dfd46e299da634954db6b4a
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153809B2

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