Iodine → ethyl 8-iodo-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

HRID 81946

反応式

HRID 81946 の反応式
N[C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1.[I-:21].[Cs+].II.N(OCCC(C)C)=O>C(COC)OC.[Cu](I)I>[I:21][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1

参加物

7

反応物 4

HCID 807IodineHCID 8053Isoamyl NitriteHCID 24601Cesium iodideHCID 24993827ethyl 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

生成物 1

HCID 44232943ethyl 8-iodo-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate収率 46%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a well stirred suspension of ethyl 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (9.0 g, 33 mmol) in dimethoxyethane (0.7 L) under N2, cesium iodide (8.6 g, 33 mmol), bisublimated iodine (4.19 g, 16.5 mmol), copper iodide (2.0 g, 10 mmol) and isopentyl nitrite (6.62 mL, 49.5 mmol) were added in sequence. The reaction mixture was stirred vigorously at 65-70° C. for 3 hours. After cooling in an ice-water bath, the solid was filtered off. The filtrate was diluted with dichloromethane (2.0 L), washed with 30% ammonium hydroxide (150 mL), sodium thiosulphate (300 mL), brine, dried over anhydrous Na2SO4 and concentrated to give 5.69 g of the title compound (46% yield).

後処理

  1. stirringThe reaction mixture was stirred vigorously at 65-70° C. for 3 hours
  2. temperatureAfter cooling in an ice-water bath
  3. filtrationthe solid was filtered off
  4. additionThe filtrate was diluted with dichloromethane (2.0 L)
  5. washwashed with 30% ammonium hydroxide (150 mL), sodium thiosulphate (300 mL), brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-bc92d3892c64466fa8b33352c03f5173
出典データセット
uspto-grants-2014_09
特許番号
US08846701B2

関連ノート

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