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 1473217ノート

反応式

HRID 1473217 の反応式
[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

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodide2 回HCID 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a6779ed0b8aa4047a843fd15aa44eeee
出典データセット
uspto-grants-2015_04
特許番号
US09012642B2

反応ノート

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