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

HRID 1691833ノート

反応式

HRID 1691833 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-3ddaee935dfd46e299da634954db6b4a
出典データセット
uspto-grants-2012_04
特許番号
US08153809B2

反応ノート

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