1,2-Dimethoxyethane → 4-(6-Chloro-4-methyl-pyridin-3-yl)-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

HRID 41685

반응식

HRID 41685 반응식
I[C:2]1[C:3](=[O:14])[CH:4]2[CH:9]([C:10]=1[O:11][CH3:12])[CH:8]1[O:13][CH:5]2[CH2:6][CH2:7]1.[Cl:15][C:16]1[N:21]=[CH:20][C:19](B(O)O)=[C:18]([CH3:25])[CH:17]=1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:15][C:16]1[N:21]=[CH:20][C:19]([C:2]2[C:3](=[O:14])[CH:4]3[CH:9]([C:10]=2[O:11][CH3:12])[CH:8]2[O:13][CH:5]3[CH2:6][CH2:7]2)=[C:18]([CH3:25])[CH:17]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 441191696-Chloro-4-methylpyridine-3-boronic acidHCID 685690024-Iodo-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

생성물 1

HCID 723324594-(6-Chloro-4-methyl-pyridin-3-yl)-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one수율 64.9%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 313Hydrochloric Acid용매

반응 조건

온도
130 °C

실험 절차

A microwave vial is charged with 4-iodo-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (184 mg, 0.6 mmol), 6-chloro-4-methylpyridine-3-boronic acid (103 mg, 0.6 mmol) and bis(triphenylphosphine)palladium dichloride (21 mg, 0.03 mmol). DME (1 ml) is added, followed by 2N aqueous sodium carbonate solution (0.6 ml, 1.2 mmol) and the reaction is heated to 130° C. by microwave irradiation, with stirring, for 30 minutes. The reaction is then diluted with 2N HCl (20 ml), extracted with ethyl acetate (20 ml), and the organic layer is removed and purified by flash chromatography on silica gel to give 4-(6-chloro-4-methyl-pyridin-3-yl)-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (119 mg).

후처리

  1. extractionextracted with ethyl acetate (20 ml)
  2. customthe organic layer is removed
  3. custompurified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-7aaa8d583ecf4c4fbab7dc484af1bd7e
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530667B2

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