Cesium carbonate → 5-(4-(Morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 336406

反応式

HRID 336406 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:21]=[CH:20][C:12]([CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=2)O1.Br[C:24]1[N:29]2[N:30]=[C:31]([NH2:33])[N:32]=[C:28]2[CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(COC)OC.O>C(OCC)(=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]>[O:17]1[CH2:16][CH2:15][N:14]([CH2:13][C:12]2[CH:11]=[CH:10][C:9]([C:24]3[N:29]4[N:30]=[C:31]([NH2:33])[N:32]=[C:28]4[CH:27]=[CH:26][CH:25]=3)=[CH:21][CH:20]=2)[CH2:19][CH2:18]1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 27955024-((Morpholino)methyl)phenylboronic acid pinacol esterHCID 18180031Water 1,2-dimethoxyethaneHCID 252159395-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

生成物 1

HCID 591864835-(4-(Morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine収率 69%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine (1.9 g, 6.3 mmol), 5-bromo-[1,2,4]triazolo[1,5-a]pyridine-2-amine (1 g, 5 mmol), 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride (250 mg, 0.63 mmol), and cesium carbonate (4.1 g, 12.6 mmol) in 10:1 dimethoxyethane/water (11 mL) was heated at 140° C. under microwave radiation for 1 h. The reaction mixture was diluted with ethyl acetate (200 mL), and the resulting suspension was filtered through celite. The filtrate was concentrated, and the resulting residue was purified by flash column chromatography (petroleum ether→ethyl acetate) to provide product (1 g, 69% yield). LCMS (ESI) m/z: 310.

後処理

  1. filtrationthe resulting suspension was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. customthe resulting residue was purified by flash column chromatography (petroleum ether→ethyl acetate)

出典と根拠

ORDレコード
ord-a2eeac91b4f04a35975b2331edd9176d
出典データセット
uspto-grants-2014_11
特許番号
US08889673B2

関連ノート

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