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2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59405022、化合物

HRID 1892188
ノート
印刷プレビュー

反応式

HRID 1892188 の反応式
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][C:7](=[O:21])[NH:8][C:9]3[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:10]=3[C:11]=2[N:12]=1.Br[C:23]1[C:24]([C:30]([F:33])([F:32])[F:31])=[N:25][CH:26]=[C:27]([Cl:29])[CH:28]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC([O-])(C)C.[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1.C(O)(C)(C)C>[Cl:29][C:27]1[CH:28]=[C:23]([NH:1][C:2]2[N:3]=[CH:4][C:5]3[CH2:6][C:7](=[O:21])[NH:8][C:9]4[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:10]=4[C:11]=3[N:12]=2)[C:24]([C:30]([F:33])([F:31])[F:32])=[N:25][CH:26]=1
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 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23665647Potassium tert-butoxideHCID 534174683-Bromo-5-chloro-2-(trifluoromethyl)pyridineHCID 59405023HCID 59405023、化合物

生成物 1

HCID 59405022HCID 59405022、化合物収率 12%

試薬・触媒・溶媒 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 6386tert-Butanol溶媒2 回
HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-amino-9-(trifluoromethyl)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (0.42 g, 1.44 mmol), 3-bromo-5-chloro-2-(trifluoromethyl)pyridine (0.37 g, 1.44 mmol), Xphos (0.054 g, 0.115 mmol), and tris(dibenzylideneacetone)dipalladium(0) (0.052 g, 0.057 mmol) in a sealed microwave tube was evacuated and purged with argon 3 times. To the vial were added tert-butyl alcohol (5.3 mL) and 1.00 M of t-BuOK in tert-butyl alcohol (2.0 mL, 2.0 mol) via syringe. The mixture was allowed to stir to mix well, then was subjected to microwave irradiation at 150° C. for 1200 sec. The mixture was allowed to cool to rt and THF (6 mL) was added. The mixture was filtered and the solid was washed with THF. The organic solutions were combined and concentrated. The residue was purified by column chromatography to give 2-{[5-chloro-2-(trifluoromethyl)pyridin-3-yl]amino}-9-(trifluoromethyl)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (0.081 g, 12%) as a solid.

後処理

  1. customwas evacuated
  2. custompurged with argon 3 times
  3. additionto mix well
  4. customirradiation at 150° C. for 1200 sec
  5. filtrationThe mixture was filtered
  6. washthe solid was washed with THF
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-8e27ee75101a46c4b5898f221b7dc860
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08507667B2

反応ノート

読み込み中…

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