Cesium fluoride → 1-(2-Methoxymethyl-3-cyclopropylphenyl)-4-methyl-1,4-dihydrotetraz ol-5-one

HRID 628494ノート

反応式

HRID 628494 の反応式
[CH3:1][O:2][CH2:3][C:4]1[C:9](Br)=[CH:8][CH:7]=[CH:6][C:5]=1[N:11]1[C:15](=[O:16])[N:14]([CH3:17])[N:13]=[N:12]1.[CH:18]1(B(O)O)[CH2:20][CH2:19]1.[F-].[Cs+]>O1CCOCC1>[CH3:1][O:2][CH2:3][C:4]1[C:9]([CH:18]2[CH2:20][CH2:19]2)=[CH:8][CH:7]=[CH:6][C:5]=1[N:11]1[C:15](=[O:16])[N:14]([CH3:17])[N:13]=[N:12]1

参加物

5

反応物 3

HCID 25953Cesium fluorideHCID 2760897Cyclopropylboronic acidHCID 898762251-(2-Methoxymethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one

生成物 1

HCID 898812581-(2-Methoxymethyl-3-cyclopropylphenyl)-4-methyl-1,4-dihydrotetraz ol-5-one収率 99.3%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A mixture of 1-(2-methoxymethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 8) 30.1 g, cyclopropylboronic acid 12.9 g, cesium fluoride 46.2 g, [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct 8.2 g and dioxane 680 ml was stirred at 90° C. for four hours. After cooling the reaction mixture, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-methoxymethyl-3-cyclopropylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one 26.0 g.

後処理

  1. temperatureAfter cooling the reaction mixture
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-2400f77e643242598c4322e66dbff0c9
出典データセット
uspto-grants-2016_04
特許番号
US09314023B2

反応ノート

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