Cesium carbonate → HCID 89586676、化合物

HRID 1747781ノート

反応式

HRID 1747781 の反応式
[CH2:1]([O:8][C:9]1[C:14](Br)=[N:13][C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([N:28]2[C:32](B3OC(C)(C)C(C)(C)O3)=[CH:31][CH:30]=[N:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.COCCOC>[CH2:1]([O:8][C:9]1[C:14]([C:32]2[N:28]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:29]=[CH:30][CH:31]=2)=[N:13][C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 580723671-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 89586067HCID 89586067、化合物

生成物 1

HCID 89586676HCID 89586676、化合物収率 104.2%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
110 °C

実験手順

A mixture of 2-(benzyloxy)-3-bromo-5-phenylpyrazine (0.17 g), 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.20 g), X-phos (24 mg), Pd2(dba)3 (11 mg), 2M aqueous cesium carbonate solution (0.62 mL) and 1,2-dimethoxyethane (5.0 mL) was stirred at 110° C. for 1 hr under microwave irradiation. The reaction mixture was cooled to room temperature, filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.21 g).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-fa2bc88bfad941808525c36585ec1054
出典データセット
uspto-grants-2015_10
特許番号
US09150588B2

反応ノート

読み込み中…