Water → 4-[6-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 2175060ノート

反応式

HRID 2175060 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16](Br)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][C:22]1([CH3:37])[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[C:28]2[CH:27]=[C:26](B(O)O)[CH:25]=[CH:24][C:23]1=2.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>COCCO.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>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:26]3[CH:25]=[CH:24][C:23]4[C:22]([CH3:37])([CH3:21])[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[C:28]=4[CH:27]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 962WaterHCID 10353857(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acidHCID 160590464-Boc-1-(6-bromo-2-pyridyl)piperazineHCID 22031701Potassium phosphate, tribasic, monohydrate

生成物 1

HCID 672487534-[6-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 80192-Methoxyethanol溶媒

反応条件

温度
80 °C

実験手順

150 mg (0.44 mmol) of 4-(6-bromopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester, 112 mg (0.48 mmol) of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylboronic acid and 202 mg (0.88 mmol) of tripotassium phosphate monohydrate are suspended in 6 ml of ethylene glycol monomethyl ether, degassed a number of times, and 25 mg (0.04 mmol) of bis(triphenylphosphine)-palladium(II) dichloride are added under nitrogen atmosphere. The reaction mixture is stirred at 80° C. for 16 h, cooled to RT, and 20 ml of water are added. This mixture is extracted three times with ethyl acetate, dried over Na2SO4 and evaporated. The crude product is purified by means of flash chromatography on silica gel.

後処理

  1. additionare added under nitrogen atmosphere
  2. temperaturecooled to RT
  3. extractionThis mixture is extracted three times with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe crude product is purified by means of flash chromatography on silica gel

出典と根拠

ORDレコード
ord-5e714a96b7684b788d884a672e756db8
出典データセット
uspto-grants-2015_06
特許番号
US09062015B2

反応ノート

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