Cesium carbonate → 2-Butyl-5-(5-phenylpyridin-3-ylamino)isoindolin-1-one

HRID 1878633ノート

反応式

HRID 1878633 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:5]2.[C:16]1([C:22]2[CH:23]=[C:24]([NH2:28])[CH:25]=[N:26][CH:27]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[CH2:12]([N:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:28][C:24]3[CH:25]=[N:26][CH:27]=[C:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:23]=3)[CH:3]=2)[C:7]1=[O:11])[CH2:13][CH2:14][CH3:15]

参加物

9

反応物 4

HCID 10796Cesium carbonateHCID 27629015-Phenylpyridin-3-amineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67432057HCID 67432057、化合物

生成物 1

HCID 534771302-Butyl-5-(5-phenylpyridin-3-ylamino)isoindolin-1-one収率 55.5%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

5-Bromo-2-butylisoindolin-1-one (71.6 mg, 0.267 mmol), 5-phenylpyridin-3-amine (50.0 mg, 0.294 mmol) and Cs2CO3 (217.0 mg, 0.668 mmol) were added to suspension of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (X-Phos) (12.7 mg, 0.027 mmol) and palladium acetate (PdOAc2) (8.0 mg, 0.040 mmol) in toluene (2 mL). The mixture was stirred and heated in the microwave (120° C., 300 W, 60 min). Water and ethyl acetate were added. The organic layer was separated, the aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over MgSO4. Purification by flash chromatography (dichloromethane/methanol, gradient 1-5% methanol) provided 2-butyl-5-(5-phenylpyridin-3-ylamino)isoindolin-1-one (53 mg, 54%). ESI-MS [M+H]+=358.1.

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. customPurification by flash chromatography (dichloromethane/methanol, gradient 1-5% methanol)

出典と根拠

ORDレコード
ord-6d499d031d8c4330b99d9c7f12944549
出典データセット
uspto-grants-2012_11
特許番号
US08314120B2

反応ノート

読み込み中…