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Triethylamine → 6-phenoxy-2-(3-{5-[1-(2-pyrrolidin-1-ylethyl)-1H-pyrazol-4-yl]-pyrimidin-2-yl}benzyl)-2H-pyridazin-3-one

HRID 2207256
ノート
印刷プレビュー

反応式

HRID 2207256 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:26]=[CH:27][CH:28]=2)[CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:13]2)=[N:6][CH:7]=1.[N:29]1([CH2:34][CH2:35][N:36]2[CH:40]=[C:39](B3OC(C)(C)C(C)(C)O3)[CH:38]=[N:37]2)[CH2:33][CH2:32][CH2:31][CH2:30]1.O.O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(N(CC)CC)C>COCCOC.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]([C:14]1[CH:15]=[CH:16][C:17](=[O:18])[N:12]([CH2:11][C:10]2[CH:26]=[CH:27][CH:28]=[C:8]([C:5]3[N:4]=[CH:3][C:2]([C:39]4[CH:38]=[N:37][N:36]([CH2:35][CH2:34][N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)[CH:40]=4)=[CH:7][N:6]=3)[CH:9]=2)[N:13]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
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

8

反応物 4

HCID 8471TriethylamineHCID 18407952Tripotassium phosphate trihydrateHCID 584970712-[3-(5-bromopyrimidin-2-yl)benzyl]-6-phenoxy-2H-pyridazin-3-oneHCID 588858611-(2-(pyrrolidin-1-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

生成物 1

HCID 468365016-phenoxy-2-(3-{5-[1-(2-pyrrolidin-1-ylethyl)-1H-pyrazol-4-yl]-pyrimidin-2-yl}benzyl)-2H-pyridazin-3-one

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

3.5 A suspension of 218 mg (0.50 mmol) of 2-[3-(5-bromopyrimidin-2-yl)benzyl]-6-phenoxy-2H-pyridazin-3-one, 251 mg (0.75 mmol) of 1-(2-pyrrolidin-1-ylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (content 87%) and 230 mg (1.00 mmol) of tripotassium phosphate trihydrate in 2 ml of 1,2-dimethoxyethane and 1 ml of DMF is heated to 85° C. under nitrogen. 35.0 mg (0.05 mmol) of bis(triphenylphosphine)palladium(II) chloride and 9 μl (0.07 mmol) of triethylamine are then added and stirred at 85° C. for 42 hours. The reaction mixture is partitioned between THF and saturated sodium chloride solution. The organic phase is dried over sodium sulfate, evaporated and chromatographed on a silica-gel column with methanol/tert-butyl ether as eluent, giving 6-phenoxy-2-(3-{5-[1-(2-pyrrolidin-1-ylethyl)-1H-pyrazol-4-yl]-pyrimidin-2-yl}benzyl)-2H-pyridazin-3-one as yellowish amorphous material; ESI 520.

後処理

  1. customThe reaction mixture is partitioned between THF and saturated sodium chloride solution
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated
  4. customchromatographed on a silica-gel column with methanol/tert-butyl ether as eluent

出典と根拠

ORDレコード
ord-9f5a11ab88e44154bc691ffc1efd2fbe
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09376426B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート