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

反応式

HRID 41685 の反応式
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

参加物

7

反応物 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

生成物 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-one収率 64.9%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 313Hydrochloric Acid溶媒

反応条件

温度
130 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-7aaa8d583ecf4c4fbab7dc484af1bd7e
出典データセット
uspto-grants-2013_09
特許番号
US08530667B2

関連ノート

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