Methyl 3-azido-6'-methoxy-6-(4-methoxyphenyl)-2,3'-bipyridine-4-carboxylate → methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxylate

HRID 2410687노트

반응식

HRID 2410687 반응식
[N:1]([C:4]1[C:5]([C:22]2[CH:23]=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)=[N:6][C:7]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[N+]=[N-]>ClC1C=CC=CC=1Cl>[CH3:29][O:28][C:25]1[N:24]=[C:23]2[NH:1][C:4]3[C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]([C:14]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=4)=[N:6][C:5]=3[C:22]2=[CH:27][CH:26]=1

참가 물질

3

반응물 1

HCID 86663008Methyl 3-azido-6'-methoxy-6-(4-methoxyphenyl)-2,3'-bipyridine-4-carboxylate

생성물 1

HCID 66605458methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxylate수율 72%

시약·촉매·용매 1

HCID 72391,2-Dichlorobenzene용매

실험 절차

A solution of methyl 3-azido-6′-methoxy-6-(4-methoxyphenyl)-2,3′-bipyridine-4-carboxylate (120 mg, 0.31 mmol) in 1,2-dichlorobenzene (4 mL) was heated at 180° C. for 10 min with gas evolution. The solvent was removed under vacuum and the product was purified by silica gel radial chromatography (step gradient elution with hexane containing 50 to 100% methylene chloride). This gave methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxylate (80 mg, 72% yield) as a yellow solid. MS (ESI) m/z 364.1 (M+H). 1H NMR (CDCl3) δ ppm 9.61 (1H, s), 8.49 (1H, d, J=8.55 Hz), 8.14 (1H, s), 8.07 (2H, d, J=8.85 Hz), 7.02 (2H, d, J=8.85 Hz), 6.73 (1H, d, J=8.55 Hz), 4.06 (3H, s), 4.04 (3H, s), 3.87 (3H, s).

후처리

  1. customThe solvent was removed under vacuum
  2. customthe product was purified by silica gel radial chromatography (step gradient elution with hexane containing 50 to 100% methylene chloride)

출처 및 근거

ORD 기록
ord-5306b336de7f4f7693afe7cde550d96f
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815840B2

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