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Dichloromethane → 5-(4-(4-(3-Fluorobenzyloxy)-3-(2-(triisopropylsilyl)ethynyl)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

HRID 877110
ノート
印刷プレビュー

反応式

HRID 877110 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=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[C:25]#[C:26][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29].[C:40]([O-:43])([O-])=O.[K+].[K+].[CH2:46](Cl)Cl.CO[CH2:51][CH2:52][O:53][CH3:54]>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:37]=[CH:38][CH:39]=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:54]4[O:53][C:52]([CH:40]=[O:43])=[CH:51][CH:46]=4)[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[CH:9][C:8]=1[C:25]#[C:26][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 67504459N-(4-(3-fluorobenzyloxy)-3-(2-(triisopropylsilyl)ethynyl)phenyl)-6-iodoquinazolin-4-amine

生成物 1

HCID 866684785-(4-(4-(3-Fluorobenzyloxy)-3-(2-(triisopropylsilyl)ethynyl)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde収率 75%

試薬・触媒・溶媒 2

HCID 44119782Bis(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 (48 mg) was added to a mixture of N-(4-(3-fluorobenzyloxy)-3-(2-(triisopropylsilyl)ethynyl)phenyl)-6-iodoquinazolin-4-amine (420 mg, 0.65 mmole), 5-formylfuran-2-yl-2-boronic acid (108 mg, 1.2 equiv.) 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 (300 mg). LCMS ESI(+) m/z: 620 (M+1). Yield: 75%.

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-8df0fbc24eef4b28b258f1592f7ee2e9
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08987284B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート