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

HRID 877104ノート

反応式

HRID 877104 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
75 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-ce6775b5025146bb877ae8d7b2c4c403
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…