Pyridine → ethyl 2-(7-(3-(hydroxymethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate

HRID 885062노트

반응식

HRID 885062 반응식
[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([CH2:14][OH:15])=[N:10]2)=[C:5]2[NH:16][CH:17]=[CH:18][C:4]=12.C([Mg]Br)C.N1C=CC=CC=1.Cl[C:30](=[O:36])[C:31]([O:33][CH2:34][CH3:35])=[O:32]>C1COCC1>[OH:15][CH2:14][C:11]1[N:12]=[CH:13][N:9]([C:6]2[N:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]3[C:18]([C:30](=[O:36])[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:17][NH:16][C:5]=23)[N:10]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 20884Ethoxalyl chlorideHCID 58026032(1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)methanolHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 58026036ethyl 2-(7-(3-(hydroxymethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate수율 71.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-40 °C

실험 절차

To a solution of (1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)methanol (70 mg, 0.285 mmol) in THF (5 mL) was added ethylmagnesium bromide (1.284 mL, 1.284 mmol) at −40° C. After stirring at −5° C. for 1H, pyridine (0.012 mL, 0.143 mmol) was added quickly. The mixture was cooled to −40° C. and ethyl 2-chloro-2-oxoacetate (0.130 mL, 1.142 mmol) was added. After stirring at −40° C. for 30 min, the reaction mixture was quenched by adding i-PrOH and water. The mixture was extracted with EtOAc (2×40 mL). The organic layers were combined, washed with brine (30 mL), dried over MgSO4 and concentrated under vacuum to give crude product ethyl 2-(7-(3-(hydroxymethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate (70 mg, 0.203 mmol, 71.0% yield). LCMS: m/z 346.1 (M+H)+, 1.42 min (method 8).

후처리

  1. additionwas added quickly
  2. customthe reaction mixture was quenched
  3. additionby adding i-PrOH and water
  4. extractionThe mixture was extracted with EtOAc (2×40 mL)
  5. washwashed with brine (30 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-81a1e40feb1b4a38ac0b11c1e0a75f2a
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242124B2

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