Cesium carbonate → HCID 57509990、化合物

HRID 624155ノート

反応式

HRID 624155 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([N:18]3[CH2:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19]3)=[O:17])=[CH:11][CH:10]=2)O1.Cl[C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32](=[O:39])[NH:31][N:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.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]>[O:39]=[C:32]1[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:29]([C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16]([N:18]3[CH2:19][C:20]4[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:26]3)=[O:17])=[CH:13][CH:14]=2)=[N:30][NH:31]1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 27751424-chlorophthalazin-1(2H)-oneHCID 68754457HCID 68754457、化合物

生成物 1

HCID 57509990HCID 57509990、化合物

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

105 mg N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)isoindoline-2-carboxamide (0.288 mmol) and 53 mg 4-chloro-1,2-dihydrophthalazin-1-one (0.288 mmol) were dissolved in 2.5 ml dioxane. Cesium carbonate (474 mg, 1.44 mmol) was dissolved in 0.25 ml water and the resulting solution added to the reaction mixture. After the addition of 27.8 mg [1,1′-bis(diphenylphosphino)-ferrocene]dichlorpalladium(II) (0.038 mmol) the reaction mixture was flushed with nitrogen and stirred for 30 minutes in the microwave (Biotage Initiator 2.5) at 110° C. Dioxane was removed under reduced pressure, water and dichloromethane added to the residue and the formed precipitation was filtered. After dissolving the solid matter in a larger amount of dichloromethane/methanol 8:2, silica gel was added and subsequently the solvent was removed under reduced pressure. This residue was was purified by column chromatography using dichloromethane/methanol 95:5. 1H NMR (DMSO-d6, 400 MHz): 6 ppm 12.73 (s, 1H), 8.55 (s, 1H), 8.33 (dd, 1H), 7.85-7.92 (m, 2H), 7.73-7.78 (m, 3H), 7.48 (d, 2H), 7.35-7.38 (m, 2H), 7.30-7.33 (m, 2H), 4.81 (s, 4H). MS (ESI(−)) m/e 383.2 (M+H)+.

後処理

  1. additionthe resulting solution added to the reaction mixture
  2. customwas flushed with nitrogen
  3. customDioxane was removed under reduced pressure, water and dichloromethane
  4. additionadded to the residue
  5. customthe formed precipitation
  6. filtrationwas filtered
  7. dissolutionAfter dissolving the solid matter in a larger amount of dichloromethane/methanol 8:2, silica gel
  8. additionwas added
  9. customsubsequently the solvent was removed under reduced pressure
  10. customThis residue was was purified by column chromatography

出典と根拠

ORDレコード
ord-a003cbd2afd243068fe6ab2a80e2c285
出典データセット
uspto-grants-2016_04
特許番号
US09302989B2

反応ノート

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