Carbon Dioxide → 7-Chloro-5-methyl-1H-pyrrolo[2,3-c]pyridine

HRID 639526노트

반응식

HRID 639526 반응식
[CH:1]([Mg]Br)=[CH2:2].[Cl:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[C:8]([CH3:15])[N:7]=1.C(=O)=O.[Cl-].[NH4+]>C1COCC1>[Cl:5][C:6]1[N:7]=[C:8]([CH3:15])[CH:9]=[C:10]2[CH:2]=[CH:1][NH:12][C:11]=12

참가 물질

6

반응물 4

HCID 280Carbon DioxideHCID 25517Ammonium ChlorideHCID 12682302-Chloro-6-methyl-3-nitropyridineHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 534878197-Chloro-5-methyl-1H-pyrrolo[2,3-c]pyridine수율 44%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Vinylmagnesium bromide solution (1 M in THF, 111 mL, 111 mmol) was added dropwise at −78° C. to a solution of 2-chloro-3-nitro-6-picoline (6.19 g, 35.2 mmol) in THF (200 mL). The dry ice cooling bath was replaced by an ice/NaCl cooling bath, and the reaction mixture was allowed to reach RT over 18 h, then the reaction mixture was carefully treated with 20% aq. ammonium chloride solution (210 mL). The reaction mixture was extracted with ethyl acetate, the organic layer was dried (MgSO4), and evaporated. Chromatography of the residue (SiO2, heptane/ethyl acetate gradient) afforded the title compound (2.58 g, 44%). Orange solid, MS (EI) 166.1 (100, M+).

후처리

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried (MgSO4)
  3. customevaporated

출처 및 근거

ORD 기록
ord-7fd3a5ed71b34d6da5fb2515eb201663
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691876B2

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