Sodium Carbonate → 3-[4-(Cyclohexyloxy)phenyl]pyrazin-2-amine

HRID 2035799ノート

反応式

HRID 2035799 の反応式
C(=O)([O-])[O-].[Na+].[Na+].[CH:7]1([O:13][C:14]2[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl[C:24]1[C:25]([NH2:30])=[N:26][CH:27]=[CH:28][N:29]=1>O.COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:7]1([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:24]3[C:25]([NH2:30])=[N:26][CH:27]=[CH:28][N:29]=3)=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 2762242-Amino-3-chloropyrazineHCID 222898184-Cyclohexyloxy-benzeneboronic acid

生成物 1

HCID 667481483-[4-(Cyclohexyloxy)phenyl]pyrazin-2-amine収率 77.8%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

A mixture of sodium carbonate (491 mg), tetrakis(triphenylphosphine)palladium(0) (80 mg), 4-(cyclohexyloxy)phenylboronic acid (612 mg) and 3-chloropyrazin-2-amine (300 mg) in water (3 mL) and DME (15 mL) was stirred at 80° C. for 4 hr. Silica gel was added and the mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give 3-[4-(cyclohexyloxy)phenyl]pyrazin-2-amine (485 mg) as a white solid.

後処理

  1. additionSilica gel was added
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

出典と根拠

ORDレコード
ord-ce29652cb9804afaa485558ed6eac362
出典データセット
uspto-grants-2013_11
特許番号
US08575154B2

反応ノート

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