Water → 2-[2-Amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-4-fluorobenzaldehyde

HRID 1631104ノート

反応式

HRID 1631104 の反応式
Br[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].O.[NH2:18][C:19]1[N:28]=[C:27]([C:29]([N:31]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32]2)=[O:30])[C:26]2[C:21](=[CH:22][CH:23]=[C:24](B3OC(C)(C)C(C)(C)O3)[CH:25]=2)[N:20]=1>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]>[NH2:18][C:19]1[N:28]=[C:27]([C:29]([N:31]2[CH2:32][C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:39]2)=[O:30])[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:2]3[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=3[CH:4]=[O:5])[CH:25]=2)[N:20]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27733192-Bromo-4-fluorobenzaldehydeHCID 58457219[2-Amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone

生成物 1

HCID 867625702-[2-Amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-4-fluorobenzaldehyde

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
120 °C

実験手順

244 mg of 2-bromo-4-fluorobenzaldehyde, 0.35 g of potassium carbonate, 4 μl of water and 98 mg of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride are added to a solution of 500 mg of [2-amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone in 12 ml of ethanol under argon. The mixture is heated at 120° C. for 4 h; then allowed to cool, during which a precipitate deposits. The precipitate is filtered off, taken up in 10 ml of ethyl acetate and washed 3 times with 10 ml of water each time. After drying over sodium sulfate, the mixture is filtered off and evaporated to dryness in vacuo; yield: 495 mg (91%) of 2-[2-amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-4-fluorobenzaldehyde; HPLC retention time: 1.73 min;

後処理

  1. temperatureto cool, during which a precipitate deposits
  2. filtrationThe precipitate is filtered off
  3. washwashed 3 times with 10 ml of water each time
  4. dry with materialAfter drying over sodium sulfate
  5. filtrationthe mixture is filtered off
  6. customevaporated to dryness in vacuo

出典と根拠

ORDレコード
ord-d6f1bd01503a4835a5c210d89418a6ee
出典データセット
uspto-grants-2014_07
特許番号
US08791129B2

反応ノート

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