Sodium Carbonate → HCID 89649230, 화합물

HRID 2207598노트

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HRID 2207598 반응식
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

참가 물질

8

반응물 3

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

생성물 1

HCID 89649230HCID 89649230, 화합물수율 32%

시약·촉매·용매 4

HCID 178419050HCID 178419050, 화합물촉매HCID 962Water용매2회HCID 6344Dichloromethane용매HCID 80711,2-Dimethoxyethane용매

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온도
120 °C

실험 절차

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);

후처리

  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

출처 및 근거

ORD 기록
ord-21a079ecbe5947ef85f20fe1af4496ee
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376436B2

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