Hydrochloric Acid → methyl 2-(1,6-dimethyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-hydroxyacetate

HRID 1473217노트

반응식

HRID 1473217 반응식
[OH:1][CH:2]([C:7]1[N:12]([CH3:13])[C:11](=[O:14])[C:10]2[NH:15][CH:16]=[CH:17][C:9]=2[C:8]=1[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)[C:3]([O:5][CH3:6])=[O:4].[C:25]([O-])([O-])=O.[Cs+].[Cs+].CI.Cl>C(#N)C.O>[CH3:25][N:15]1[C:10]2[C:11](=[O:14])[N:12]([CH3:13])[C:7]([CH:2]([OH:1])[C:3]([O:5][CH3:6])=[O:4])=[C:8]([C:18]3[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=3)[C:9]=2[CH:17]=[CH:16]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodide2회HCID 10796Cesium carbonateHCID 89473317methyl 2-hydroxy-2-(6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate

생성물 1

HCID 89463238methyl 2-(1,6-dimethyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-hydroxyacetate수율 101.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

A suspension of methyl 2-hydroxy-2-(6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate (30 mg, 0.092 mmol) and Cs2CO3 (35.9 mg, 0.110 mmol) in Acetonitrile (1 mL) was treated with MeI (6.90 μL, 0.110 mmol) and heated to 50° C. for 3 hours. Additional MeI (10 uL) was added, the reaction was stirred at 50° C. for 3 hours. The mixture was cooled to rt, diluted with water, acidified with 1N HCl, extracted with EtOAc 3×, washed with brine, dried with Na2SO4, filtered, and concentrated. Combined with crude product from the same reaction (0.040 mol scale) and purified with column chromatography (0-100% EtOAc/Hexane) to give methyl 2-(1,6-dimethyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-hydroxyacetate (31.7 mg, 0.093 mmol, 70.6% yield) as clear oil. LCMS (m/z) ES+=341 (M+1).

후처리

  1. temperatureThe mixture was cooled to rt
  2. extractionextracted with EtOAc 3×
  3. washwashed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customCombined with crude product from the same reaction (0.040 mol scale)
  8. custompurified with column chromatography (0-100% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-a6779ed0b8aa4047a843fd15aa44eeee
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012642B2

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