Cesium carbonate → 2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridine

HRID 1920032

反応式

HRID 1920032 の反応式
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:6]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]3[O:22][CH2:21][CH2:20][O:19]3)=[CH:14][CH:13]=1)=[N:7]2.CC1(C)C(C)(C)OB([C:37]2[CH:38]=[N:39][N:40](C(OC(C)(C)C)=O)[CH:41]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)(O)[O-].[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:19]1[CH2:20][CH2:21][O:22][CH:18]1[C:15]1[CH:14]=[CH:13][C:12]([C:6]2[C:5]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:4][C:3]3[C:8](=[CH:9][CH:10]=[N:11][C:2]=3[C:37]3[CH:38]=[N:39][NH:40][CH:41]=3)[N:7]=2)=[CH:17][CH:16]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 575007255-Chloro-2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-1,6-naphthyridine

生成物 1

HCID 575007242-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridine

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 5-chloro-2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-1,6-naphthyridine (1-1, Reference: WO2006135627A2, Dec. 21, 2006) (1.7 g, 4.2 mmol) in DMF (100 mL) was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (2.5 g, 8.6 mmol), cesium carbonate (4.2 g, 13 mmol) and Pd(Ph3P)2Cl2 (0.030 g, 0.042 mmol). The reaction mixture was heated at 100° C. under an atmosphere of N2 for 1 hour. The reaction was cooled to room temperature, poured into saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum. Purification by silica gel chromatography (EtOAc in hexane) gave 2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridine (1-2) as a white solid. MS (M+H)+: calculated 421.47; found 421.51

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification by silica gel chromatography (EtOAc in hexane)

出典と根拠

ORDレコード
ord-8ce21cb9f7d948ce949108a88dd9e60a
出典データセット
uspto-grants-2012_05
特許番号
US08168652B2

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