Potassium Carbonate → (5-(4-(4-((3-Fluorobenzyl)oxy)-3-chloroanilino)-6-quinazolinyl)-2-furancarboxaldehyde

HRID 877080ノート

反応式

HRID 877080 の反応式
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26](I)[CH:27]=3)[N:22]=[CH:21][N:20]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1.[O:30]1[CH:34]=[CH:33][CH:32]=[C:31]1B(O)O.[C:38]([O-])([O-])=[O:39].[K+].[K+]>[Pd].CCO.COCCOC>[Cl:2][C:3]1[CH:4]=[C:5]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:34]4[O:30][C:31]([CH:38]=[O:39])=[CH:32][CH:33]=4)[CH:27]=3)[N:22]=[CH:21][N:20]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 2734357Furan-2-boronic acidHCID 66623345[3-Chloro-4-(3-fluorobenzyloxy)phenyl](6-iodoquinazolin-4-yl)amine hydrochloride

生成物 1

HCID 11181296(5-(4-(4-((3-Fluorobenzyl)oxy)-3-chloroanilino)-6-quinazolinyl)-2-furancarboxaldehyde

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
75 °C

実験手順

A mixture of [3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-(6-iodo-quinazolin-4-yl)-amine hydrochloride salt (5.05 g, 10 mmol), 2-furylboronic acid (1.85 g, 12 mmol) and palladium catalyst (730 mg, 1.0 mmol) in 10 mL of K2CO3(2.0M), 10 mL of EtOH and 40 mL of DME was heated at 75° C. under nitrogen atmosphere for 4 hr. LS-MS showed the reaction completed. Concentrated the mixture under reduced pressure and washed the residue with water (2×50 mL) then with cool ether (100 mL) to get a gray solid (4.5 g), which was used for next step without further purification.

後処理

  1. concentrationConcentrated the mixture under reduced pressure
  2. washwashed the residue with water (2×50 mL)

出典と根拠

ORDレコード
ord-255313f93ab0470eabb9fc3f6e909dbb
出典データセット
uspto-grants-2015_03
特許番号
US08987284B2

反応ノート

読み込み中…