Triphenylphosphine → 1-(4-nitro-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide

HRID 384975

反応式

HRID 384975 の反応式
[O:1]=[C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][NH:3]1.[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:21]=1[CH2:22][CH2:23][C:24]2=O)([O-:19])=[O:18].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CN(C=O)C.O>[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:21]=1[CH2:22][CH2:23][CH:24]2[N:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:9])[C:2]1=[O:1])([O-:19])=[O:18]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 905634-Nitroindan-1-oneHCID 35448842-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamideHCID 5363146Diisopropyl azodicarboxylate

生成物 1

HCID 498038661-(4-nitro-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide収率 21%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (8.0 g, 1.0 eq) in dry DMF (30 mL) was added 4-nitro-2,3-dihydro-1H-inden-1-one (1.2 eq) and PPh3 (3.0 eq), then added DIAD (3.0 eq) under N2 atmosphere. Then the mixture was stirred at room temperature overnight. At the end of reaction, water was added and extracted with ethyl acetate. The combined organic layer was washed with brine and dried over MgSO4, filtrated and evaporated to give the crude product, which was purified by Flash Column (PE:EtOAc=1:2), concentrated the crude product, and recrystallized by EtOAc to give 1-(4-nitro-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (3.5 g, 21%). MS (ESI) 377.0 (M+H); 1H NMR (300 MHz, CDCl3) δ 12.22 (s, 1H), 8.62 (m, 1H), 8.53 (m, 2H), 8.24 (m, 1H), 7.67 (m, 2H), 7.49 (m, 2H), 6.75 (m, 1H), 6.50 (m, 1H), 3.71 (m, 1H), 3.57 (m, 1H), 2.97 (m, 1H), 2.21 (m, 2H).

後処理

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltrated
  6. customevaporated
  7. customto give the crude product, which
  8. customwas purified by Flash Column (PE:EtOAc=1:2)
  9. concentrationconcentrated the crude product
  10. customrecrystallized by EtOAc

出典と根拠

ORDレコード
ord-c5832e318d6e4d9ba22e7f70daa9f1c3
出典データセット
uspto-grants-2013_02
特許番号
US08367836B2

関連ノート

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