Sodium hydride → HCID 22024972, 화합물

HRID 1792817노트

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HRID 1792817 반응식
[H-].[Na+].[CH:3]1([C:6]2[C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][NH:9][CH:10]=2)[CH2:5][CH2:4]1.Cl[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[CH:18][CH:17]=1>CN(C)C=O.[Cl-].[Na+].O>[CH:3]1([C:6]2[C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][N:9]([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=[CH:18][CH:17]=3)[CH:10]=2)[CH2:4][CH2:5]1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 691404-ChloroquinolineHCID 22024944Methyl 4-cyclopropyl-1H-pyrrole-3-carboxylate

생성물 1

HCID 22024972HCID 22024972, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 57417360Sodium chloride; water용매

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온도
40 °C

실험 절차

0.208 g (6.5 mmol) of sodium hydride at 75% by weight in liquid petroleum jelly is added to a solution of 1.07 g (6.5 mmol) of 4-cyclopropyl-3-methoxycarbonyl-1H-pyrrole in 20 mL of dimethylformamide at a temperature in the region of 20° C. under an argon atmosphere. After the reaction mixture has been stirred at a temperature in the region of 40° C. for 0.3 hour, 1.07 g (6.5 mmol) of 4-chloroquinoline and 10 mL of dimethylformamide are added. After stirring for 6 hours at a temperature in the region of 120° C., the reaction mixture is poured into 200 mL of brine and then extracted with 100 mL and then 50 mL of ethyl acetate. The organic extracts are combined and then concentrated to dryness under reduced pressure (2.7 kPa). The oily residue is purified by chromatography on silica gel [eluent: dichloromethane/ethyl acetate (75/25 by volume)]. After the fractions containing the expected product have been concentrated to dryness under reduced pressure (2.7 kPa), 1.2 g of 4-cyclopropyl-3-methoxycarbonyl-1-(quinolin-4-yl)-1H-pyrrole are obtained in the form of a thick clear oil, which is used directly in the following step.

후처리

  1. stirringAfter stirring for 6 hours at a temperature in the region of 120° C.
  2. extractionextracted with 100 mL
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe oily residue is purified by chromatography on silica gel [eluent: dichloromethane/ethyl acetate (75/25 by volume)]
  5. additionAfter the fractions containing the expected product
  6. concentrationhave been concentrated to dryness under reduced pressure (2.7 kPa), 1.2 g of 4-cyclopropyl-3-methoxycarbonyl-1-(quinolin-4-yl)-1H-pyrrole
  7. customare obtained in the form of a thick clear oil, which

출처 및 근거

ORD 기록
ord-0ef7b04f28b2421da6aa4ad91d5e166b
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07078414B2

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