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p-Bromochlorobenzene → N-(4-chlorophenyl)-5-(4-(morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 336407
ノート
印刷プレビュー

反応式

HRID 336407 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]4[N:20]=[C:21]([NH2:23])[N:22]=[C:18]4[CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.Br[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.C(OCC)(=O)C.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]>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([NH:23][C:21]2[N:22]=[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([C:11]4[CH:12]=[CH:13][C:8]([CH2:7][N:4]5[CH2:3][CH2:2][O:1][CH2:6][CH2:5]5)=[CH:9][CH:10]=4)[N:19]3[N:20]=2)=[CH:26][CH:27]=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 7806p-BromochlorobenzeneHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 591864835-(4-(Morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

生成物 1

HCID 59186222N-(4-chlorophenyl)-5-(4-(morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine収率 44.7%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

A suspension of 5-(4-(morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (0.50 g, 1.6 mmol), 1-bromo-4-chlorobenzene (340 mg, 1.8 mmol), tris(dibenzylideneacetone)dipalladium (0) (147 mg, 0.16 mmol), cesium carbonate (782 mg, 2.4 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (94 mg, 0.16 mmol) in 1,4-dioxane (50 mL) was heated to reflux for 2 days. The reaction mixture was diluted with ethyl acetate (300 mL), and the resulting suspension was filtered though celite. Concentration of the filtrate in vacuo provided crude product, which was purified by flash column chromatography (petroleum ether→ethyl acetate) to give product (300 mg, 44% yield). LCMS (ESI) m/z: 421.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 2 days
  3. filtrationthe resulting suspension was filtered though celite
  4. customConcentration of the filtrate in vacuo provided crude product, which
  5. customwas purified by flash column chromatography (petroleum ether→ethyl acetate)

出典と根拠

ORDレコード
ord-adc6cebc29b64eae9f7868b2ce961408
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08889673B2

反応ノート

読み込み中…

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