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Potassium Fluoride → Ethyl 2-fluoro-4-[6-(1-trityl-1H-pyrazol-4-yl)-quinazolin-4-yl]benzoate

HRID 1792609
ノート
印刷プレビュー

反応式

HRID 1792609 の反応式
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([F:23])[CH:13]=1.[C:24]([N:43]1[CH:47]=[C:46](B(O)O)[CH:45]=[N:44]1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[F-].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CN(C)C=O>[F:23][C:14]1[CH:13]=[C:12]([C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:46]4[CH:45]=[N:44][N:43]([C:24]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)[C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)[CH:47]=4)[CH:3]=3)[N:8]=[CH:7][N:6]=2)[CH:22]=[CH:21][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 522689Potassium FluorideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 22031224Ethyl 4-(6-chloroquinazolin-4-yl)-2-fluorobenzoateHCID 22031737(1-Trityl-1H-pyrazol-4-yl)boronic acid

生成物 1

HCID 22031192Ethyl 2-fluoro-4-[6-(1-trityl-1H-pyrazol-4-yl)-quinazolin-4-yl]benzoate収率 70.1%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

0.64 g ethyl 4-(6-chloroquinazolin-4-yl)-2-fluorobenzoate (compound in Production Example 385), 1.02 g 1-trityl-1H-4-pyrazolylboronic acid, 0.34 g potassium fluoride, 43 mg palladium (II) acetate, 0.11 g 2-(di-t-butylphosphino)biphenyl, 20 mL N,N-dimethylformamide and 2 mL water were heated at 70° C. for 24 hours under nitrogen atmosphere. Water was added thereto, the reaction solution was filtered, and crystals collected by filtration were washed with water. The crystals were dissolved in dichloromethane, washed with water and dried over sodium sulfate. The solvent was evaporated, and the residue was purified by NH silica gel column chromatography (hexane/ethyl acetate), to give 0.82 g of the title compound (pale yellow crystals).

後処理

  1. filtrationthe reaction solution was filtered
  2. filtrationcrystals collected by filtration
  3. washwere washed with water
  4. dissolutionThe crystals were dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by NH silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-a7c568d94a0f4e84ae663770a21c8249
出典データセット
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07074801B1

反応ノート

読み込み中…

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