Water → 1-Methyl-5-(4-pyridinylamino)-1H-indole

HRID 5891

반응식

HRID 5891 반응식
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[NH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[CH:14]=[CH:13]2.O.C(=O)([O-])[O-].[Na+].[Na+]>CN1CCCC1=O>[CH3:19][N:15]1[C:16]2[C:12](=[CH:11][C:10]([NH:9][C:3]3[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=3)=[CH:18][CH:17]=2)[CH:13]=[CH:14]1

참가 물질

6

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 818524-Chloropyridine hydrochloride2회HCID 27695641-methyl-1H-indol-5-amine

생성물 1

HCID 98159221-Methyl-5-(4-pyridinylamino)-1H-indole수율 53.3%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

4-Chloropyridine hydrochloride (8 g) was added to a solution of 5-amino-1-methylindole (7 g) in 75 ml 1-methyl-2-pyrrolidinone preheated to 100° C. The addition of 4-chloropyridine hydrochloride (4 g) after one hour caused no further reaction as determined by TLC. After two hours the reaction mixture was cooled, stirred with water, basified with sodium carbonate and extracted with ethyl acetate. The dried (anhydrous magnesium sulfate) organic layer was filtered and evaporated to 12.7 g of an oil. The oil was eluted through silica with 10% methanol in dichloromethane via flash column chromatography to give the product which was triturated with ether to yield 5.7 g of a solid, m.p. 202°-203° C. Recrystallization from acetonitrile yielded 5 g of product as crystals, mp 209°-211° C.

후처리

  1. custompreheated to 100° C
  2. customno further reaction
  3. temperatureAfter two hours the reaction mixture was cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialThe dried (anhydrous magnesium sulfate) organic layer
  6. filtrationwas filtered
  7. customevaporated to 12.7 g of an oil
  8. washThe oil was eluted through silica with 10% methanol in dichloromethane via flash column chromatography
  9. customto give the product which
  10. customwas triturated with ether

출처 및 근거

ORD 기록
ord-5f7c51d628ad4fcda89d3d4a2d4eafae
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246947

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