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

HRID 81946

반응식

HRID 81946 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bc92d3892c64466fa8b33352c03f5173
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846701B2

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