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Potassium Carbonate → 5-(4-(3-Chloro-4-(pyridin-2-ylmethoxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

HRID 877086
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인쇄 미리보기

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HRID 877086 반응식
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25](I)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1B(O)O.[C:37]([O-])([O-])=[O:38].[K+].[K+]>[Pd].CCO.COCCOC>[Cl:2][C:3]1[CH:4]=[C:5]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:33]4[O:29][C:30]([CH:37]=[O:38])=[CH:31][CH:32]=4)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2734357Furan-2-boronic acidHCID 68153209[3-Chloro-4-(2-pyridylmethoxyl)-phenyl]-(6-iodo-quinazolin-4-yl)-amine hydrochloride salt

생성물 1

HCID 874249045-(4-(3-Chloro-4-(pyridin-2-ylmethoxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

시약·촉매·용매 3

HCID 23938Palladium촉매
HCID 702
Ethanol
용매
HCID 80711,2-Dimethoxyethane용매

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온도
75 °C

실험 절차

A mixture of compound 8.3 (489 mg, 1.0 mmol), 2-furylboronic acid (185 mg, 1.2 mmol) and palladium catalyst (73.0 mg, 0.10 mmol) in 1.0 mL of K2CO3 (2.0M), 1.0 mL of EtOH and 4.0 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 (2×5.0 mL) then with cool ether (10.0 mL) to get a gray solid (400 mg), which was used for next step without further purification.

후처리

  1. concentrationConcentrated the mixture under reduced pressure
  2. washwashed the residue with water (2×5.0 mL)

출처 및 근거

ORD 기록
ord-ae9d60f09a4f4ad2a023ef63d479a528
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08987284B2

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