Sodium Hydroxide → Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate

HRID 1500675노트

반응식

HRID 1500675 반응식
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH:12]=O)=[N:6][C:5]=1[Cl:14].O(Cl)Cl.[P+5].[OH-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:6]([CH:12]=[N:11][CH:10]=2)[C:5]=1[Cl:14])=[O:15]

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 583245442-Chloro-6-formylaminomethylnicotinic acid methyl esterHCID 178479711HCID 178479711, 화합물

생성물 1

HCID 58324565Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate수율 88%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
65 °C

실험 절차

To a suspension of 2-chloro-6-formylaminomethylnicotinic acid methyl ester (42.6 g, 0.19 mol) in toluene (400 mL) was added phosphorous (V) oxychloride (18.2 mL, 0.20 mol) and the reaction mixture heated at 65° C. for 1.5 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (200 mL) before treating with sodium hydroxide solution (2 M) to adjust pH˜8. The layers were separated and the aqueous layer extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine (100 mL), dried (MgSO4) then charcoal (˜5 g) was added and the solution mixed for 5 minutes before being filtered and concentrated in vacuo to yield the title compound as a tan solid (34.4 g, 88%) 1H NMR (CDCl3, 400 MHz) 8.52 (1H, s), 7.57 (1H, s), 7.45 (1H, d, J=9.3 Hz), 7.25 (1H, d, J=9.1 Hz), 3.97 (3H, s).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with ethyl acetate (2×100 mL)
  4. washThe combined organic extracts were washed with brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. additioncharcoal (˜5 g) was added
  7. additionthe solution mixed for 5 minutes
  8. filtrationbefore being filtered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-186b0584fe4f4f8bb20dbfbc51ed03ce
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206174B2

반응 노트

불러오는 중…