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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(2,4-dichlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one

HRID 2102874
ノート
印刷プレビュー

反応式

HRID 2102874 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:17]2[CH2:16][CH2:15][N:14]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:13](=[O:24])[C:12]=2[C:11]([CH3:25])=[C:10]1[C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:17]2[CH:16]=[CH:15][N:14]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:13](=[O:24])[C:12]=2[C:11]([CH3:25])=[C:10]1[C:26]1[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 166661651-(2,4-Dichlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-4-one

生成物 1

HCID 578035911-(2,4-dichlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one収率 49%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A suspension of 1-(2,4-dichlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (153 mg, 0.325 mmol) and DDQ (295 mg, 1.301 mmol) in 1,4-dioxane (12 ml) was stirred at rt for 1 h and 20 min followed by 1 h and 50 min at 35° C. and 2 h and 50 min at 45° C. The solvent was evaporated and the product purified by hplc. The solvent was evaporated and water added. The product was extracted from the water phase with DCM and EtOAc. The combined organic phases were evaporated and the residue was re-suspended in toluene and evaporated to yield the product as a yellow solid (74 mg, 49%). MS m/z 468 (M+H)+.

後処理

  1. waitfollowed by 1 h and 50 min at 35° C. and 2 h and 50 min at 45° C
  2. customThe solvent was evaporated
  3. customthe product purified by hplc
  4. customThe solvent was evaporated
  5. additionwater added
  6. extractionThe product was extracted from the water phase with DCM and EtOAc
  7. customThe combined organic phases were evaporated
  8. customevaporated

出典と根拠

ORDレコード
ord-24c20c684d464bbf9755b32c204ad5ad
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07576095B2

反応ノート

読み込み中…

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