1,4-Dioxane → 3-(Benzylthio)-8-(2-methoxy-4-(trifluoromethyl)phenyl)-1,7-naphthyridine

HRID 1473493ノート

反応式

HRID 1473493 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1B(O)O.[CH2:16]([S:23][C:24]1[CH:25]=[N:26][C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[N:29][C:28]=2Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>C(C1C(C(C)(C)C)=C([Pd]Cl)C=CC=1NC)(C)(C)C.O>[CH2:16]([S:23][C:24]1[CH:25]=[N:26][C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[N:29][C:28]=2[C:4]1[CH:5]=[CH:6][C:7]([C:9]([F:12])([F:11])[F:10])=[CH:8][C:3]=1[O:2][CH3:1])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

7

反応物 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 24901776(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acidHCID 866875473-(Benzylthio)-8-chloro-1,7-naphthyridine

生成物 1

HCID 866875483-(Benzylthio)-8-(2-methoxy-4-(trifluoromethyl)phenyl)-1,7-naphthyridine収率 91.1%

試薬・触媒・溶媒 2

HCID 178482226HCID 178482226、化合物触媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

To a vial charged with 2-methoxy-4-(trifluoromethyl)phenyl boronic acid (Combi-Blocks, San Diego, Calif.) (0.268 g, 1.216 mmol), 3-(benzylthio)-8-chloro-1,7-naphthyridine (0.218 g, 0.760 mmol), and potassium phosphate tribasic (0.189 ml, 2.280 mmol) was added dioxane (3.05 ml) and water (1.016 ml). The mixture was purged with argon prior to the addition of 1,1-bis[(di-t-butyl-p-methylaminophenyl]palladium(II) chloride (0.054 g, 0.076 mmol). The vessel was sealed and heated to 60° C. overnight. After cooling to ambient temperature, the mixture was loaded directly onto a silica gel loading column and purified with a 40 g HP spherical column (silicycle) (SiliCycle, Inc. Quebec City, Canada) ramping EtOAc in heptane (0 to 35%, then isocratic at 35%) to provide 3-(benzylthio)-8-(2-methoxy-4-(trifluoromethyl)phenyl)-1,7-naphthyridine (0.295 g, 0.692 mmol, 91% yield) as an off-white foam. m/z (ESI) 427.3 (M+H)+.

後処理

  1. customThe mixture was purged with argon
  2. customThe vessel was sealed
  3. temperatureAfter cooling to ambient temperature
  4. custompurified with a 40 g HP spherical column (silicycle) (SiliCycle, Inc. Quebec City, Canada)

出典と根拠

ORDレコード
ord-803a6665c1c84f96943080ff028c4d2c
出典データセット
uspto-grants-2015_04
特許番号
US09012443B2

反応ノート

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