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

HRID 249247ノート

反応式

HRID 249247 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-390bfbd4ffbb43649e1c3e14ef2ef26e
出典データセット
uspto-grants-1993_05
特許番号
US05214038

反応ノート

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