Sodium Carbonate → HCID 89649230、化合物

HRID 2207598ノート

反応式

HRID 2207598 の反応式
Br[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH2:13][CH2:12][C:11]3([CH2:17][CH2:16][N:15]([CH3:18])[C:14]3=[O:19])[N:10]=2)[CH:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:29]=2[C:30]#[N:31])O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.ClCCl.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:8][C:6]1[CH:7]=[C:2]([C:28]2[CH:35]=[C:34]([C:36]([F:37])([F:39])[F:38])[CH:33]=[CH:32][C:29]=2[C:30]#[N:31])[CH:3]=[C:4]([C:9]2[CH2:13][CH2:12][C:11]3([CH2:17][CH2:16][N:15]([CH3:18])[C:14]3=[O:19])[N:10]=2)[N:5]=1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 569731072-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzonitrileHCID 89649623HCID 89649623、化合物

生成物 1

HCID 89649230HCID 89649230、化合物収率 32%

試薬・触媒・溶媒 4

HCID 178419050HCID 178419050、化合物触媒HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
120 °C

実験手順

To a solution of 2-(4-bromo-6-methyl-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one (which may be prepared as described in Description 13) (180 mg, 0.5600 mmol) in 1,2-dimethoxyethane (3 mL) and water (1 mL) was added 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzonitrile (182.56 mg, 0.6100 mmol) and sodium carbonate (177.65 mg, 1.68 mmol). The reaction mixture was degassed with nitrogen and then treated with bis(triphenylphosphine)palladium (II) dichloride (19.61 mg, 0.0300 mmol). The reaction was heated in the microwave at 120° C. for 15 minutes. The reaction mixture was diluted with dichloromethane and water. After separation of the layers, the aqueous phase was re-extracted with dichloromethane and the combined organic phases passed through a hydrophobic frit. The solvent was evaporated and the residue purified by silica gel chromatography to afford 2-[2-methyl-6-(7-methyl-6-oxo-1,7-diazaspiro[4.4]non-1-en-2-yl)-4-pyridyl]-4-(trifluoromethyl)-benzonitrile (D14) as a colourless solid (74 mg);

後処理

  1. customThe reaction mixture was degassed with nitrogen
  2. customAfter separation of the layers
  3. extractionthe aqueous phase was re-extracted with dichloromethane
  4. customThe solvent was evaporated
  5. customthe residue purified by silica gel chromatography

出典と根拠

ORDレコード
ord-21a079ecbe5947ef85f20fe1af4496ee
出典データセット
uspto-grants-2016_06
特許番号
US09376436B2

反応ノート

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