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

HRID 877080노트

반응식

HRID 877080 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
75 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-255313f93ab0470eabb9fc3f6e909dbb
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987284B2

반응 노트

불러오는 중…