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1H-Pyrazol-3-amine, 5-methyl- → 2-Isopropyl-4-(5-methyl-1H-pyrazol-3-ylamino)-7-(2-methylsulfanyl-ethoxy)-2H-phthalazin-1-one

HRID 1783712
ノート
印刷プレビュー

反応式

HRID 1783712 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH2:14][S:15][CH3:16])=[CH:9][CH:10]=2)[C:5](=[O:17])[N:4]([CH:18]([CH3:20])[CH3:19])[N:3]=1.CC(C)([O-])C.[Na+].[NH2:27][C:28]1[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)C>[CH:18]([N:4]1[N:3]=[C:2]([NH:27][C:28]2[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=2)[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH2:14][S:15][CH3:16])=[CH:9][CH:10]=2)[C:5]1=[O:17])([CH3:20])[CH3:19]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 689794224-Bromo-2-isopropyl-7-(2-methylsulfanyl-ethoxy)-2H-phthalazin-1-one

生成物 1

HCID 247534922-Isopropyl-4-(5-methyl-1H-pyrazol-3-ylamino)-7-(2-methylsulfanyl-ethoxy)-2H-phthalazin-1-one収率 23.4%

試薬・触媒・溶媒

2
HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
100 °C

実験手順

Degassed toluene (6 ml) and EtOH (3 ml) were added in one portion to a mixture of 4-bromo-2-isopropyl-7-(2-methylsulfanyl-ethoxy)-2H-phthalazin-1-one (0.3 g, 0.8 mmol), sodium t-butoxide (0.112 g, 1.2 mmol), 3-amino-5-methyl pyrazole (0.107 g, 1.2 mmol), tris-(dibenzylideneacetone)-dipalladium (0.038 g, 0.042 mmol) and 2-(di-t-butylphosphino)-biphenyl (0.025 g, 0.084 mmol) under nitrogen. The reaction mixture was heated to 100° C. for 20 hours with stirring and then cooled to RT. Diethyl ether (10 ml) was added and the precipitated solid was filtered to give the crude product as a grey solid. Flash column chromatography (elution: 95% EtOAc, 5% MeOH) afforded the title compound as a white solid (0.070 g, 7% yield).

後処理

  1. customDegassed toluene (6 ml) and EtOH (3 ml)
  2. temperaturecooled to RT
  3. filtrationthe precipitated solid was filtered
  4. customto give the crude product as a grey solid
  5. washFlash column chromatography (elution: 95% EtOAc, 5% MeOH)

出典と根拠

ORDレコード
ord-be436706b01948fcb9adab5d833f4aae
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07501410B2

反応ノート

読み込み中…

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