Dichloromethane → 5-(4-(4-(3-Fluorobenzyloxy)-3-bromophenylamino)quinazolin-6-yl)furan-2-carbaldehyde

HRID 877104노트

반응식

HRID 877104 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21](I)[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[CH:9][C:8]=1[Br:25].[C:29]([O-:32])([O-])=O.[K+].[K+].[CH2:35](Cl)Cl.CO[CH2:40][CH2:41][O:42][CH3:43]>C(O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:43]4[O:42][C:41]([CH:29]=[O:32])=[CH:40][CH:35]=4)[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[CH:9][C:8]=1[Br:25]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 21874791N-(4-(3-fluorobenzyloxy)-3-bromophenyl)-6-iodoquinazolin-4-amine

생성물 1

HCID 218747965-(4-(4-(3-Fluorobenzyloxy)-3-bromophenylamino)quinazolin-6-yl)furan-2-carbaldehyde수율 89%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 702Ethanol용매

반응 조건

온도
75 °C

실험 절차

Under nitrogen atmosphere, Pd(dppf)2Cl2 (80 mg) was added to a mixture of N-(4-(3-fluorobenzyloxy)-3-bromophenyl)-6-iodoquinazolin-4-amine (550 mg, 1 mmole), 5-formylfuran-2-yl-2-boronic acid (170 mg, 1.2 mmole) and 2M K2CO3 (4 mL) in Ethanol (4 mL) and DME (4 mL). The reaction mixture was heated at 75° C. for 4 h and cooled down to room temperature. Methylene chloride (30 mL) was added and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography, eluting with 20% methanol in dichloromethane to give the desired product as white solid (460 mg). LCMS ESI(+) m/z: 519 (M+1). Yield: 89%.

후처리

  1. temperaturecooled down to room temperature
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 20% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-ce6775b5025146bb877ae8d7b2c4c403
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987284B2

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