1,4-Dioxane → Methyl 4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylate

HRID 1253568노트

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HRID 1253568 반응식
I[C:2]1[N:6]2[C:7]([O:17][CH3:18])=[CH:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[C:29]([C:32]([O:34][CH3:35])=[O:33])[S:30][CH:31]=2)O1.C(=O)(O)[O-].[Na+].O1CCOCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:18][O:17][C:7]1[N:6]2[C:2]([C:27]3[CH:28]=[C:29]([C:32]([O:34][CH3:35])=[O:33])[S:30][CH:31]=3)=[CH:3][N:4]=[C:5]2[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=1

참가 물질

7

반응물 4

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 52911233Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylateHCID 584048583-Iodo-5-methoxy-7-phenylimidazo[1,2-a]pyridine

생성물 1

HCID 58404681Methyl 4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylate

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매

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온도
90 °C

실험 절차

3-iodo-5-methoxy-7-phenylimidazo[1,2-a]pyridine (166 mg, 0.474 mmol), methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (254 mg, 0.948 mmol), tetrakis(triphenylphosphine)palladium (0) (55.0 mg, 0.047 mmol), and sodium bicarbonate (150 mg, 1.42 mmol) were added to a dry flask. Dioxane (5 ml) and water (0.5 ml) were added and the reaction mixture was sparged with argon for 3 minutes. The reaction mixture was heated to 90° C. After 6 h the reaction mixture was cooled to ambient temperature, diluted with ethyl acetate, washed with water, then dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/dichloromethane gradient) to give methyl 4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylate. LRMS (ESI) calculated for C20H17N2O3S [M+H]+, 365.1 found 365.0.

후처리

  1. customthe reaction mixture was sparged with argon for 3 minutes
  2. temperatureAfter 6 h the reaction mixture was cooled to ambient temperature
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (ethyl acetate/dichloromethane gradient)

출처 및 근거

ORD 기록
ord-7b2be4d79f0e4c4fbb6c612050161090
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455477B2

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