Isopropanol → N-(3-Fluoro-4-pyridinyl)-3-methyl-1H-indol-1-amine

HRID 440430노트

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HRID 440430 반응식
C(O)(C)C.Cl.Cl[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[F:13].[CH3:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([NH2:24])[CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>O>[F:13][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:7]=1[NH:24][N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([CH3:14])=[CH:16]1

참가 물질

6

반응물 4

HCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 124272923-Methyl-1H-indol-1-amineHCID 193602344-Chloro-3-fluoropyridine hydrochloride

생성물 1

HCID 9942843N-(3-Fluoro-4-pyridinyl)-3-methyl-1H-indol-1-amine수율 63.7%

시약·촉매·용매 1

HCID 962Water용매

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온도
90 °C

실험 절차

To 200 ml isopropanol was added 4-chloro-3-fluoropyridine hydrochloride (10 g) and 3-methyl-1H-indole-1-amine (5.9 g). The mixture was stirred at 90° C. for four hours, cooled; then poured into 500 ml iced-water, pH adjusted to 10 with Na2CO3 solution, then extracted with ethyl acetate. The organic layer was washed with water, then dried (saturated NaCl, anhydrous MgSO4). After filtering, the solvent was evaporated to an oil, which was eluted on a silica gel column with CH2Cl2 (DCM) then with ether:petroleum ether (1:1) via flash chromatography. The desired fractions were combined then evaporated to yield 6.2 g of a solid, 45° C. A sample of this material was recrystallized from isopropyl ether/hexanes (1:1) to give a solid, m.p. 141°-142° C.

후처리

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  5. filtrationAfter filtering
  6. customthe solvent was evaporated to an oil, which
  7. washwas eluted on a silica gel column with CH2Cl2 (DCM)
  8. customThe desired fractions were combined then evaporated

출처 및 근거

ORD 기록
ord-4994497ef44540bbaba22e149bf03124
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05519131

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